33 Sales Leaders on Building and Scaling a Successful Sales Team

When building a sales team, it's incorrect to assume that hiring more salespeople will equal more revenue. 

First, the duties of each role and how success will be measured should be well thought out and documented. Based on that, new hires must be placed in positions they’re well suited for in relation to their skills and ambitions. Furthermore, new applicants should fit within the culture of their sales team and the company as a whole. 

But this only scratches the surface when it comes to building an all-star sales team. We heard from 33 sales managers who shared how they grew their teams while positioning employees for career success. 

 

 

ReviewTrackers’ VP of Sales Jeff Pearlman said despite aggressive hiring goals, the customer feedback software platform only brings a new salesperson onboard if all hiring managers are a “hell yes.” This ensures that they only hire top performers who are highly self-motivated. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

It all starts with hiring the right people. We look for people who are curious, collaborative and competitive. Our culture avoids micromanagement at all costs, which means the people we hire must be autonomous and highly self-motivated. To build on those strengths, we make sure we have the right training and support system in place so that every rep has the correct tools and training to succeed. We also have a scaling compensation plan that rewards over-achievers as well as a clear career progression plan to make sure the team knows exactly how to earn promotions. 

Most of this was identified by myself and my sales management team based on successes and failures in previous roles. For example, in one of my past jobs I saw multiple top performing reps who had exceeded their quota be placed on performance management for not making enough calls. These double standards never made sense to me, and they were a driving force behind how we look at metrics.

 

"Our culture avoids micromanagement at all costs, which means the people we hire must be autonomous.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

The key is to make sure we have the right support system in place. When we started our hiring push this year, we evolved our training model from a scrappy, startup-based new hire training model to a comprehensive curriculum, which included several weeks of training from multiple leaders from across the company. We are also fortunate to have a great group of individual contributors who are highly competitive but also help each other and share sales best practices. This model allows new reps to have mentors while they continue their ongoing training.

When it comes to hiring, we follow the mentality of “it’s either a hell yes or it’s a no.” This is hard to do in a tough market with aggressive hiring goals but as long as we stick to this, we know we will bring on the right people and not sacrifice our culture.

 

Have you ever struggled to find your keys, with no recollection or roadmap to even narrow down the search (did you leave them in the kitchen or on your desk)? Onna helps you find what you’re looking for, no matter where “it” is, within  a digital landscape. We recently spoke with Russ Grant, VP of revenue, about why understanding how they support businesses is key in growing their sales team. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

There is no blueprint, unfortunately. Each company needs to understand its market, buyer and internal team, and base their hiring plan off of those audiences. We serve such a huge potential market. Near-term, we are focused on building value for mission-critical applications for legal, compliance and IT teams and companies.

Building a team at our stage is truly about diversity. Different approaches to the sales process, ways of thinking about the industry and team interaction all play into our hiring decisions. 

 

"Training, onboarding and culture are all constantly a work in progress.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

We’ve set out with a plan for scale. How do we support a business a thousand times our current size? This helps us make decisions in context and set expectations for the amazing people we’re bringing on. 

Training, onboarding and culture are all constantly a work in progress. We don’t pretend to have a perfect mold. We’re also building an international team, so we have to simultaneously look for ways to integrate and enable every employee for success. Even if it’s a new role, we ask employees what they feel they need to succeed.

 

 

On the BetterCloud sales team, success isn’t an individual sport. Chief Revenue Officer Christopher Jones told us how their leaders constantly improve their skills based on what has worked well for the team in the past. Additionally, a competition-based structure helps fuel employees’ fire to keep the SaaS operations management platform aglow. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

I believe that being a positive, high-energy servant leader is the most effective blueprint to building consistently high-performing sales teams. We have an extreme passion for winning, ensuring our teams relish the grind required to do so consistently. We have a strong team of sales leaders who are committed to coaching their direct reports to be sales champions. We value representatives who are relentless about winning, embrace a growth mindset, practice self-discipline, are team players and have a desire to be truly extraordinary. We look for examples of these traits throughout the interview process. When those candidates apply them here, success is pretty much a certainty.  

 

"We have a ‘best is the standard’ sales culture.’’ 

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Earlier this year, we hired a superstar named Meredith Dowd to lead, further develop and strengthen our onboarding and ongoing enablement program. Under her leadership, we have added quite a bit of rigor, consistency and scale to BetterCloud’s sales excellence programs. 

We are dedicated to putting all the required enabling conditions in place to get and keep our teams on the leading edge of sales practices. We have a “best is the standard” sales culture. We celebrate firsts, personal bests, new sales records, wins and leadership performances in a big way. 

Our top performers have a strong yet friendly rivalry so they always keep their edges sharp. Consistent communication is a huge tenant of my scaling growth playbook. This includes weekly sales leaderboard update emails, extended team hangouts, ongoing town hall sessions and our top performers sharing their best-of-the-best practices. 

 

Happy Returns partners with retailers to make customers’ product-returns easy.

Co-founder and CEO David Sobie said that spirit of cooperation is also taken up by the company’s sales and marketing teams, who collaborate relentlessly to drive value for the business. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

We have a playbook that wins, with a focused go-to-market strategy, clear segmentation and targeting, and defined roles and responsibilities.

Having a leader who sets the bar high is important. Who do sales professionals want to be like as their careers progress? Someone that prioritizes strategy execution, keeps the team on target, is tied at the hip with the marketing and customer success teams and who brings crucial field information back to company leadership.

We also hire people with a history of high performance, a passion for our mission and a competitive drive to win. Emotional intelligence and IQ are equally important. A knowledge of the industry is also a plus.

 

"Having a leader who sets the bar high is important.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

We obsess over the basics. We have weekly pipeline reviews, one-on-ones and shadowings. The marketing team attends our important meetings and we attend theirs. We also have monthly messaging and content syncs for sales training. Everything we do comes back to your values. Is the team complaining about prospect and customer demands? Then it’s time to revisit our strategy.

And we make sure to have fun. We joke with each other a ton and have holiday potlucks, monthly happy hours and Friday themed days. 

We look for empathy among our friends, doctors and therapists. But films like “The Wolf of Wall Street” depict that characteristic as having little to no place in business or finance. A peek inside the sales teams of three Seattle tech companies tells a different story. 

Hiring and training the right people for the job came up again and again in our conversations –– a strategy not to be confused with hiring the best individual seller or the most enthusiastic. While attitude and credibility is crucial in any role, you want your front line of defense to be straightforward and trustworthy, from their first interaction with a client to their last.

 

MVF Global’s platform helps 120 companies make sales by delivering new customers through cross-channel marketing. Charlie Parkin, head of sales, America, told us that developing The Sales Academy, a three-month training program for new hires, gives employees the confidence and tools they need for success. 

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

We’ve hired passionate people ever since we launched the U.S. office with the landing team and it’s something we haven’t compromised on since. We’re able to maintain a culture of success — a team who is here to build something, not just take a paycheck.

Naturally, we’ve had to build more process into hiring and training as we’ve grown. We’ve developed a comprehensive three-month training program for new starters called The Sales Academy. It combines experiential, relationship training and research-based learning, along with post-graduation weekly learning sessions for the broader team. 

 

"All team members help each other toward a common goal: team and individual success.” 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

The first key to success is to inspire. We are pushing the team to do more than they thought possible, while inspiring a culture of “more than just quota” This focus on building something as a team instead of defining people by their numbers has helped us achieve pretty epic growth.

We also believe in teaching. We don’t hire for outright skill, but potential. All team members help each other toward a common goal: team and individual success.

We learned that what gets measured gets done. We give the team the tools to measure their own success easily and set clear initiatives. We’re a data-driven organization, and our ability to visualize and understand sales trends has helped both our retention and individuals’ performance.

 

 

Matthew Cappello, regional vice president of sales at Rapid7, knows his audience. He leverages sales employees’ competitive natures to create an environment that’s challenging but supportive. 

Their insight cloud offers customers full visibility into their connected environment, providing analytics and automation so that users can focus on their business’s main mission rather than thwarting cyber attacks. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

Our three fundamentals are our investments in our people, sales enablement and process. It really starts with hiring and attracting the right talent. We have found that sales representatives with high levels of self-awareness give our teams the ability to be more prescriptive with both our sales enablement engine and management techniques.  

It takes the guesswork out of individual development plans and creates a trusting environment for representatives to take disciplined risks knowing that management will throw the rope back over.

Lastly, sales is a numbers game. Utilizing internal and external sales tools, we baseline and track progress so each representative knows where they stand at any point in time; not only from a numbers perspective but also in terms of individual development. 

 

"We look to empower our managers and representatives to carry on the company’s core values.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

When scaling teams, it is imperative to have a shared common mission. It creates a culture of teamwork regardless of whether you’re an individual contributor or sales manager. We look to empower our managers and representatives to carry on the company’s core values.

We also recognize that effective sales training is not a one-shoe-fits-all approach. Each seller who joins Rapid7 is at a different stage in their journey and each stage requires a different approach. We pride ourselves on being flexible and adapting to the requirements of our sellers in order to provide relevant training based on their skill sets. We have a coach-first mentality, which creates a trusting relationship throughout the organization. 

Recognize that most sales representatives are inherently competitive. We encourage and promote as much healthy competition as we can. From pipeline competitions to enablement pitch offs, we try to keep the sales floor as entertaining as possible, driving a better work experience.

 

Kevin Kearns, senior vice president of Grubhub’s restaurant network, said the food delivery platform’s sales team is all about recreating success.

By documenting and repeating certain key processes — like seeking specific traits in applicants and developing a playbook of best sales practices — the sales staff is able to hire talented individuals and set them up for successful futures at the company.

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

In the past year we doubled our sales organization. Our goal is achieving both efficiency and effectiveness throughout the sales organization. For efficiency, we have removed barriers that get in the way of selling time, eliminated red tape to get deals done and set metrics that our teams need to achieve each day.

For effectiveness, we have streamlined our sales process to be consultative and value-focused, created a detailed playbook based on best practices of our top sellers and built a recognition program that keeps our teams energized each day. To round it out, we have built a culture of excellence, which includes recognition programs celebrating top performers and specific performances, and created a sales council that address areas of opportunity on behalf of their colleagues.

We executed a discovery process and identified key areas of opportunity across areas like sales process, market coverage and many others. We identified issues in each category and prioritized our action plans based on what had the biggest impact. We also structured our management team to be primarily focused on rep development.

"Hires now get a full month of onboarding and hands-on coaching...”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

Instead of hiring the way we always did, we needed to figure out how to bring on talented individuals at scale. To do that, we evaluated the traits of our best sellers and created a hiring profile and interview process that was replicable and increased the likelihood of a great fit. Once on board, instead of ad hoc training and shadowing, we reinvented the training process to be more effective. Our new hires now get a full month of onboarding and hands-on coaching, which is significantly more robust than in the past. We also invested in our trainers, all of whom have been successful sellers at Grubhub. The data shows our new hires are more productive than ever and we have reduced turnover in the first six months.

In terms of culture, we bring all new sellers into our headquarters to observe first-hand the winning attitude of our team. We then pair sellers with mentors that exhibit the habits of success within our team. Finally, we constantly reinforce the cultural attributes that make our team great: teamwork, professionalism, high performance, effort, fun and customer obsessed.

 

Information processing takes on a whole new meaning when you consider machine learning and artificial intelligence. Take, for example, AlphaSense’s AI-powered search engine. It enables businesses to access data-driven insights in seconds. Looking for a comprehensive view of AlphaSense’s hiring process and scaling methods? Vice President of Sales Enablement Alea Homison has that and more, below. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

Our blueprint begins with a robust interview process that allows us to identify and attract the best talent. We focus on core characteristics we know make people successful at AlphaSense: grit, coachability and curiosity. Our interview process, which includes assignments, helps us to clearly identify each of these characteristics. 

Once individuals join the AlphaSense family, our sales enablement efforts set them up for success throughout their entire career, from our onboarding and performance ramp programs to our ongoing sales effectiveness program while they remain here and become a vet.

"Learning is so core to our culture...’’ 

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

We have an amazing culture that we are exceptionally proud of. Instead of focusing on protecting it, we focus on adding to and growing it over time. That said, we have sales enablement programs (onboarding, new hire performance ramp and ongoing sales effectiveness) that help us scale our training programs and provide consistent support for our sales team. Learning is so core to our culture that our investment in the professional development of our employees is inherent to our DNA. We have fun as we work hard by creating initiatives and friendly competitions in unique formats. 

 

What happens when you have hiring and onboarding processes that are documented every step of the way and are repeatable across dozens of offices spread across three continents?

According to Director of Sales John Huelskamp, you get Flexport’s standardized (and effective) method of hiring and training new salespeople. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

We have had to adapt our blueprint as we’ve transitioned through many phases of growth. But the five key tenets of this blueprint are our people, process, goals, enablement and culture. Hiring talented people requires a deep understanding of the unique qualities and characteristics that lead to success at a company. We prioritize candidates that are personable, intelligent and coachable. We also look for candidates that demonstrate grit, tenacity and passion.

Over the years, we’ve continued to refine our sales process so that it’s clear, repeatable, data-driven and supported by the right tools and systems. Similarly, employee goals need to be clear, realistic and aligned with company objectives. When goals are set correctly, you reward top performers and maintain a high level of motivation across your team.

 

"We try to create as many coaching opportunities for new hires as possible.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

We’re constantly trying to improve how we onboard, train and enable our new hires to have as much success as possible. Learning styles can vary, so we blend classroom-style training during a new hire’s first few weeks in “Flexport Academy” with local enablement through a curriculum that covers departments across our LA office. 

We try to create as many coaching opportunities for new hires as possible, so our sales culture emphasizes shadowing, role-playing and team-selling. We also encourage collaboration more than competition. 

 

CrowdStrike is a cybersecurity firm that specializes in cloud-based endpoint protection. Jack Hyer, director of corporate sales, said supporting new hires in their training helps his team stay aligned with the company vision. 

 

What’s your blueprint for building a sales teams? How do you identify these keys and how have they made an impact as you build a team?

Building a high-performing sales team starts with outlining the vision you have for the team and then providing the tools and support needed for them to succeed. Another important element is culture. Purposefully fostering your culture around the behaviors and values your organization finds important gives you the framework to determine who is the best team fit and how they can best work together. For me, this means finding people who are courageous, curious and creative. 

After hiring the right people, I like to lead by example and support new hires through active participation in their early sales calls, shadowing and consistent one-to-one feedback.

"We also take great care in maintaining a positive culture...”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

Our sales leadership team believes it is better to hire the right person a little late than the wrong person too early. To ensure a positive culture that supports the industrious, entrepreneurial people we are trying to find and grow, we make sure we’re being thoughtful about our hiring decisions and that we aren’t moving too quickly. We also take great care in maintaining a positive culture and fostering our “one team, one fight” mentality. 

We do that through team building, support, office events, prospecting projects and group outings to help us build a cohesive team working toward the same goals. In seeing CrowdStrike’s Austin team grow from 26 to 90+ employees, I think we’ve struck the right balance as our team is stronger and better than ever. And we have a lot of fun, too.

 

This female-founded, mission-led startup is reinventing job training and educational opportunities for America’s workforce using their online platform.

Senior Vice President of Sales Karina Salenieks said that hiring diverse teammates is essential to creating a winning team at Guild Education.

 

What’s your blueprint for building a sales team? 

The first step in building out a team from scratch is ensuring we have the right functions to represent all parts of the sales process.  All good sellers have the “art” of the sales but the best ones blend in the “science” — the sequence of events, the repeatable steps and the diagnostics that help both them win the deal and the client get what they need.

Different perspectives help us see around corners and grow as a team with particular strengths. It’s also important to cultivate a culture that allows us to operate and win together as a team. As we scale up, deliberate onboarding is critical to ensure both speed and quality, as well as productivity.  

"...our clients win by finding a solution that truly solves their challenges...”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Write it down! We have grown so big so quickly that we can no longer rely on the expertise in one person’s head to serve as a resource. We have aligned up and down the organization in terms of who we are and what we mean to our buyers so that we all have the same North Star.

To some extent, let the culture create itself. It’s natural to see that culture evolves as the team expands and important to not get precious about it. As long as the principles of teamwork, doing right by our clients and being good citizens of Guild are there, the right aspects remain in tact.  

The company wins by our team hitting our sales goals and our clients win by finding a solution that truly solves their challenges and propels them into best-in-class organizations. The sales people win by exceeding their goals, honing their craft and being part of a winning team at a critical stage of growth.

 

Wowza Media Systems provides customizable and scalable technology solutions that simplify media streaming on any device. 

Renee Ingenito, head of global sales, explained why it’s important to reinforce and refine the company pillars while scaling her sales team. 

 

What’s your blueprint for building a sales team? 

The blueprint for building and scaling a successful sales team consists of creating a foundation with our four basic pillars: develop a sales team structure; establish a sales process of managing the pipeline in a CRM; set sales activity metrics and revenue goals; and train the team on a sales methodology.

After many years of managing sales teams, I have learned that if you are off base or falling short in one of these key four areas, your team will feel it and it will affect your success. Your sales team structure should align with your business needs and the needs of your customers. It is important to set clear expectations with your sales team and make sure they understand their targets whether it’s revenue, activity or specific objectives. 

It’s important to give your team the tools and training to do their jobs most effectively. A sales methodology sets a team up for success. It provides a consistent way in which they should approach every prospect and manage the stages of every sale to uncover customer needs and solve customer problems that result in winning new business. 

"Create the team that everyone wants to be a part of.” 

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

To maintain a successful sales organization once you’ve scaled, you must constantly reinforce and refine your four pillars. It’s important to gather, analyze and draw conclusions from the sales data you’ve collected to better define your sales best practices and to redefine how your team achieves targets. In analyzing the sales data, you will uncover parts of the business that need improvement and you will find trends and indicators regarding large wins and losses. 

A sales manager has the personal responsibility to invest in each individual on the team and be a co-owner in their success to drive overall team success. Create the team that everyone wants to be a part of with your four pillars, enthusiasm and a great work ethic.

 

Datadog is mission-first and mission focused. Petra Ross-Raymond, director of sales development, told us that their blueprint for scaling the department relies on a solid foundation. 

The monitoring service abides by the theory that increased system visibility leads to further success. And at Datadog, that applies to their culture and their product. Just check out their aggregated metrics and events DevOps stack. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

My blueprint starts with a clear mission, preferably developed as a team and influenced by key business partners. The most rewarding teams I’ve been a part of work with a sense of purpose; we can see how our efforts impact the greater goal. Foster a culture of knowledge-sharing to level up everyone’s skills and multiply your impact as a group. Look for opportunities to work closely with other roles who share your mission. 

As you scale, you may need to evolve. Be prepared to ask, “Does our mission still align to important greater goals? How are we collaborating with each other and with our business partners?”

"The most rewarding teams I’ve been a part of work with a sense of purpose.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Once you’re part of a successful team, you want to maintain what’s working. However, scale does require flexibility. High-performing teams will thrive through change when the team is aligned to a mission, when they understand how and why strategy is changing, and when they have a clear sense of what new skills or activities will be required for success.

 

Director of Sales Development Brian Mullin said Sprout Social wants its sales team to do more than meet quotas. The company wants staff to feel like they have a voice, and feel comfortable making their opinions heard.

To that end, Mullin said employee feedback at the social media management platform is incorporated into everything from training to building company culture.

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

Building a successful team starts with identifying key traits your top performers exemplify. We articulate a vision for our people that inspires them to do their best work and reach for more than they thought was possible. Every person on our team has a unique reason for choosing Sprout to start or continue their career, but regardless of the reason, that commitment is something we value and show gratitude for.

"We base our hiring processes, training and culture off of the feedback from our employees.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

The strength of our culture is foundational to why our people love coming to work everyday and it’s important that our individual contributors feel like they have a voice in the decisions we make as a business. We focus on encouraging feedback across all levels of the organization. When team members are able to openly share their thoughts and ideas, it promotes trust, drives innovation and strengthens their commitment to doing their best work. We base our hiring processes, training and culture off of the feedback from our employees — if they aren’t bought in then it’s all for naught.

 

VP of Sales in the Americas Dan Costanzo said building an atmosphere of trust and continuous learning at pricing software company Pricefx is the key to sales success. And that goes for sales leaders as well as new account execs. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

I look for self-empowered individuals who demonstrate a sense of urgency and a passion for delivering value to customers. In doing so, they reap not only personal success, but also a high degree of professional satisfaction in being part of a collective effort felt by customers, colleagues and the market. The best way to identify these characteristics is by gaining a sense of candidates’ professional values and personal initiative. 

"The best way to learn and grow as a professional is through learning from my peers.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

Ensure that candidates are well-grounded in the values of the founders. I have always believed that the best way to learn and grow as a professional is through learning from my peers, so building an atmosphere of trust and continuous learning is very important to me.

 

A quarterback can’t succeed if they’re told to act as a team’s punter. BigTime Software’s Senior VP of Sales Michael Morrison believes that putting people in positions where they can succeed based on their skills is key to building a successful sales team.

In order to do that, he said it’s first necessary to determine the specific skills needed for success in each role. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

When I build a sales team, I always start by researching and quantifying targets. Understanding who prospects are, where to find them and how to best engage with them is essential to organizing the most effective team. 

Based on over 20 years of experience in sales, I believe the second step is putting the right people in the right roles by establishing the critical skills and competencies for each position on the team. This ensures that you are hiring, training and evaluating talent based on the most relevant criteria.

The final step is execution and iteration based on the key performance indicators of the business. Are team members achieving their goals? Why or why not, and what can leaders do to help? 

"A formula of regularly celebrating wins while learning from losses helps to foster an open and transparent culture.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

This is accomplished by putting people first. Whether it’s training or hiring, you must establish practices that ensure that you hire individuals based on the right criteria and that you are providing them with the environment and the resources to be successful. This, along with a formula of regularly celebrating wins while learning from losses, helps to foster an open and transparent culture where people can contribute, develop and grow as the organization scales.

 

Commercial Sales Manager Jordan Gorosh and other leaders at Navan encourage their sales teams to put both themselves, and the customers, first.

Gorosh said users of the business travel booking platform are a priority and striving to meeting their needs is a foundational value. However, employees are also pushed to invest in their own professional needs by advancing their skills through the company’s continual learning framework.

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

The DNA of any sales team is built on its people and we place a strong emphasis on making sure each person is a cultural fit for the organization. Our core value of putting the user first is tied intrinsically to our sales team, and its leaders cascade that value throughout the team early and often. As we’ve grown and scaled our team to match that growth, keeping our users top-of-mind ensures we’re finding the right people who will own our mission and beliefs.

"We center our teams around the concept of continuous learning...”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?We center our teams around the concept of continuous learning, accountability, real-time feedback and personal reflection. Each Navan employee is trained to use our debriefing and continual learning framework to ensure that no matter how fast we’re moving, we’re taking the time to learn for our own sakes and the sake of the business. 

 

If you’re interested in underwater hockey or needlepoint-based crafts, it turns out you’re not alone. At Meetup events across the country, people can (and do) come together to pursue their interests and make connections with like-minded individuals. While that concept isn’t exactly a tough sell, Enterprise General Manager JD Singh told us how the sales team effectively gets clients through the funnel.  

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team? 

Setting up clear processes and objectives is extremely important when building a highly efficient sales team. Ambiguity leads to misunderstanding, poor results and unhappy people. Having a clear process helps the teams learn quickly and achieve concrete results. Tracking the appropriate metrics tied to objectives and setting up a solid incentive system aligned with those objectives will lead to efficient teams who execute.

"Culture and focus are key factors in scaling any team.’’ 

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Culture and focus are key factors in scaling any team. A sales machine needs to not only develop the ability to get clients through the funnel efficiently, but also  get sales representatives ramped up efficiently. Being data-driven and tracking how the team is doing on both fronts helps identify problems earlier.

 

In a perfect world, DigitalOcean Director of Inside Sales Ken Dooley sees managers treating new hires with the same level of consideration and necessary guidance as if they were direct reports. The sales division at the open-source cloud software company ensures that everyone is fully on board as the team forges new paths, an approach that is especially crucial amid rapid growth. 

 

What’s your blueprint for building a sales team? 

I like to follow some guiding principles like “define your key outcomes” from the start. Let those drive every decision the team makes. Establish the “how” with clear guidelines to help the team as they work toward those desired outcomes. 

Finally, ensure everyone really understands the key outcomes and has what they need to achieve individual and team goals. Hire amazing people with diverse backgrounds and perspectives and ensure they have what they need to be successful.

 

How did you identify these keys and how have they made an impact as you build a team?

These key principles are the result of my own learning, iterating, and course correcting  throughout the years. I’ve been lucky enough to have managers and mentors who encouraged me to take risks and not be afraid to fail. Innovation comes from failure.

I try to encourage the same kind of self-direction and autonomy with accountability on my own teams. I strongly believe that if you’ve taken the time to hire the right person and you set them up for success with clear outcomes, you have to give them the space to learn and flourish. That said, it is critical that poor performance is identified and managed quickly. 

"I’ve been lucky enough to have managers and mentors who encouraged me to take risks...’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Don’t throw out the things that have worked previously just because your team is growing. When you scale, it’s important that team leads and hiring managers uphold the same key principles through their hiring, onboarding, training and coaching practices. While not every new hire will be your direct report, they are still on your team. Ensure every new person has the same level of understanding and clarity about the key outcomes and guidelines.

 

Identity theft is a phenomenon that unfortunately pretty much everyone can relate to. But worse than having to cancel your credit card? Having your tech stack compromised. Auth0 is dedicated to making that an issue of the past, with an identity solution that’s easy to implement and customize. VP/GM Ghazi Masood told us how he authorizes top talent for the business. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

First, assess market segments and geographies that require focus. Next, hire professionals who come from credible software organizations with track records for success. Additionally, hone in on key traits such as tenacity, drive, hunger and being a team player, which are paramount in building an A-team. 

"Hire professionals who come from credible software organizations with track records for success.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

We should never sacrifice the amount of investment being made during the hiring and onboarding process. We take this quite seriously and feel we have a blueprint for one of the most thorough onboarding programs in the industry. Additionally, we foster a promote-from-within culture where the individuals can clearly see what lies ahead and what metrics and benchmarks are needed for career advancement.

 

When you work in the legal industry, there are a lot of files to review (sometimes terabytes of data for a single case). DISCO created an intuitive platform enhanced with AI predictive coding to speed up the review process, letting lawyers optimize their time.

Vice President of Lead Generation and Inside Sales Tim Alvarez said that sticking to DISCO’s core values (think continuous learning and collaboration) when hiring enhances their company culture. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

Finding the right people is key. We evaluate candidates not only on their skills and potential, but also on their eagerness to learn, collaborate and help ramp up future hires. You want to build a team that is proud to work together. If a person has a damaging effect on the rest of the team, they’re not a good hire.

Once the right people are in place, it is important to start everyone on the same page, ensuring each employee receives the training and development needed to help them reach their full potential.    

"...you must stay focused on your core hiring values...”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? Put another way, how do you scale your training and hiring processes and your culture alongside your team?

Listen to your people. Stay close to your team and pay extra attention to what the senior members tell you is key for consistency. As you scale, you must stay focused on your core hiring values and continue to bring in the right people, as they will be your future leaders. 

At DISCO, bringing in great hires enhances our culture of learning and collaboration. Together, we celebrate our successes and challenge each other to even greater achievements, benefitting both the professional development of the individual and the growth of our business.

 

AlertMedia’s emergency communications platform helps its customers monitor potential threats and streamline employee safely. Chief Revenue Officer Brett Andrew described the company as one that puts its customers first. That means hiring a sales team aligned with their company values.

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

AlertMedia puts our customers first, so we hire people and build processes that reflect who we want to be on every interaction: responsive, thoughtful, conversational, prescriptive and a trusted resource to the organizations that need our help communicating during emergency events. This requires our sales team to focus beyond the science of selling and embrace the art needed to skillfully assist thousands of prospects during their evaluations of our software. 

Our customer-centric approach has governed the blueprint for building every team in our company. This has resulted in the development of a sales team that’s fully aligned with our other departments, company goals and overall culture. 

"...we never quit leading by example...”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

AlertMedia has successfully doubled its business every year because growth to us doesn’t mean simply putting new people in more chairs. Rather, it’s about empowering new contributors to reach or achieve the success of those before them. 

We’ve accomplished that type of growth because we never quit leading by example. All tenured employees contribute to a culture focused on rolling up our sleeves to show how things are done. We encourage new leaders to step forward, while we invest heavily in the processes and support required to onboard and elevate new members of the sales team. 

We also work hard to keep everything simple, avoiding the common trap of overcomplication that often arrives with success. And we commit to transparency.

 

Frontsteps’ software platform allows community residents to engage with their homeowners association, project management consultants, builders and security companies all in one place. 

Senior Manager of Business Development Jeff Dunn explained how investing in a training and development team helps new salespeople find a home at Frontsteps.

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

For our fast-growing software-as-a-service company that’s serving the residential association space, we look for sales representatives that want to grow their professional sales career, have a proven track record and have experience working at a smaller startup. Because we are an established startup with thousands of customers and millions of dollars in annual revenue, we have lots of opportunities for professional sales representatives to grow their careers and even move into leadership opportunities. 

Although our products have been in existence for many years, we still maintain the startup atmosphere as we rapidly develop new products and acquire complementary businesses to integrate into our platform.

"Our training programs involve product, sales skills and personal development.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? Put another way, how do you scale your training and hiring processes and your culture alongside your team?

“Develop our people” is the first core value for our company. Because of this, we have invested in a new training and development team. Our training programs involve product, sales skills and personal development.

 

When your company is a leader in cloud-based risk management solutions, some of the same risk-management solutions apply when building a sales team.

Senior Vice President of Sales and Marketing Rob Patrick broke down the “secret sauce” for scaling the sales team at KPA.

 

What’s your blueprint for building a sales team? 

Everyone has their own “secret sauce” for what makes their teams great. KPA focuses on achieving the right blend of strategy and execution. First, we get crystal clear on where we’re headed as a business and the opportunities available to our ever-expanding team. 

Next, we thoughtfully hire talented people and give them the knowledge, support and tools they need to be successful. The final piece is structured effort. Being great at sales requires execution with deliberate purpose, persistence and resilience.

"...it becomes increasingly important to communicate effectively and transparently.”  

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Everyone at KPA is unique yet we all share the same passion for the work we do on behalf of our clients. As we scale the team and internal processes to support growth objectives, it becomes increasingly important to communicate effectively and transparently.  

We encourage open dialogue and feedback throughout the organization so voices are heard and people have the opportunity to influence future decisions. To achieve our future growth objectives, we must continue to think about how we can improve.

 

 

Red Canary helps companies of any size fight cyber attacks. Vice President of Sales Sergei Leonov shared how keeping core values flexible creative during growth periods is crucial when expanding a sales team.

 

What’s your blueprint for building a sales team? 

As with most things in life, there is no perfect blueprint for building a sales team. Myriad factors need to be considered such as product maturity, addressable market, go-to-market strategy and much more. In fact, sales team organization and composition should be considered iterative as your company grows and changes over time. 

However, some concepts can be useful at any stage to ensure a happy, healthy and productive sales organization. Consider what your sales team's culture and values should be. These can often be tied back to the company's mission and should help you identify some core behavioral competencies that will be important in building out the team. 

Try to align individual contributors into cross-functional teams and encourage collaboration to foster creativity, competition and camaraderie. Ensure you're building a diverse team by seeking out professionals from different backgrounds and walks of life to maximize your team's creative output and resiliency. 

"Ensure you're building a diverse team by seeking out professionals from different backgrounds...”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

While core values are fundamental to maintaining team culture during growth, it's important to be flexible and creative when scaling the team. The precise elements of your team at one stage may not work for a sales team at a later stage. 

If you've managed to build a diverse team of curious, driven and collaborative professionals, they will help you scale the organization while maintaining the core team values. Fostering transparency and trust within your team, as well as in your enablement and hiring practices, will set the right tone for sustainable growth. 

 

The path from your apartment to the building’s laundry room isn’t the only place you’ll find five steps. We recently spoke with Tom McNulty, VP of sales at Fundera, who outlined how his team stays on course and continues to grow using distinct categories of achievement. Fundera is a marketplace for small business financial solutions that’s making big strides.

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

If you are building a sales organization within a company, I have found that there are five steps to focus on. These include learning and development, repeatability, continued growth, profitability and horizontal expansion. At the beginning, don’t set robust targets. Hire industry professionals to speak to customers. Determine whether you can make your process repeatable while you implement compensation plans and workflows that you need in order to scale. 

During this stage, you will see a slight shift in growth. Simultaneously, hire traditional sales people versus industry experts and look at the long-term value of the system that has been set up. Lastly, utilize the process. Can you open up your organization to offering other product lines?

"Every organization needs to determine when sales is its own function.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Every organization needs to determine when sales is its own function. For example, at Fundera, we have sales development, sales operations and sales training in order to ensure that our sales function continues to grow and thrive. I do not believe that culture scales. I believe that culture shifts and you define your team based on that. You must effectively navigate the culture; not scale it. Keep what works and discard what doesn’t.

 

For online merchants, ShipStation compiles all shipping errands in an easy-to-use web interface, making the process efficient and less stressful. Director of Sales Cody DeArmond said that creating thorough documents for onboarding helps new hires feel as informed as he did when he was a rookie.

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

We consistently look for individuals that can raise the average of our team. When you are going through periods of hyper-growth and need six new reps ASAP, it can be tempting to lower your hiring standards. By holding out for candidates with the empathy to relate to our users on a personal level, we've been able to grow our team while constantly improving our user experience from the first interaction with ShipStation, which in turn drives increased sales. 

"We consistently look for individuals that can raise the average of our team.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

When I started at ShipStation, ramp was easy because any time I had a question, the person on either side of me was an expert and had been here since the beginning. As we've grown, ShipStation has invested heavily in documenting our processes in a way that's easily digestible for new hires so we can maintain that tribal knowledge without depending on physical proximity.

 

 

Culture is a reflection of not only the people who deliberately create it, but also anyone who contributes to a company as it grows. But culture isn’t the only thing leadership at SmartSense by Digi monitors.

The IoT solution allows users to track food and pharmacy safety and supply chain visibility. VP of Global Sales Jeff Melvin told us how his team mirrors the business’s overall vision and drives quality control.  

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

We are looking for people who want to be part of the adventure that comes with building a growth-stage technology company. This includes self-starters, motivated, passionate people who want to be part of a fun, dynamic and ever-changing environment. Employees need to fit into the culture that has been created while adding their own fingerprint. We look for team players who strive to make others around them as successful as they’ve become.

"We look for team players who strive to make others around them as successful as they’ve become.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Scaling requires a clear understanding of roles and responsibilities, as well as a defined selling process that will drive the most success while enabling people to thrive using the skills they have brought to the table. Training is constant, as change is constant. Finding people who thrive in that culture is key. A constant drumbeat of hiring must be part of the culture or the sales team won’t be able to accomplish the growth that the business demands.

 

From bartending to real estate, 360training.com provides training for over 4 million customers so they can get the jobs they want. Vice President of Sales Kevin Schoch said one of the most critical components to building a successful sales team is cultivating an atmosphere of trust.

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

I’ve been a part of many teams, from small startups to companies in the Fortune 500. The best ones always have a foundation of trust. You have to trust that your manager supports you, that your team will help you and that you have a voice.

I like to build teams with diverse backgrounds to bring new ideas and perspectives that will make the team better and ultimately, help us deliver better solutions for our customers. As a sales leader, I also love competition. I want to surround myself with people who want to win and who hold themselves accountable as much as the business does.

To uncover these skills, you really need to dig into what people have done before. Why did they choose their past roles? How did they succeed compared to others? What did they learn along the way? Where are they looking to go next in their careers? At the end of the day, I want to create an environment that allows people to accomplish more than they ever thought possible. 

 

"We want our employees to know that they have a voice...”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

 I’m looking for people who want to scale their careers. That doesn’t happen unless the business grows. If you hire people with that outlook, it’s easier to scale things like training and process along the way.

Everyone should focus on the way we run our business today while also keeping an eye on where we want to be in the future and how to get there. If something is preventing you from getting to that next stage, speak up so we can add training or adjust processes.

We ask everyone to speak up if they see a problem. It’s one of our core values. We want our employees to know that they have a voice and encourage them to use it to impact positive change and growth for the business.

 

We all have an area code or number memorized for the purpose of being able to ignore yet another telemarketer.

Alyce is on a mission to turn that annoyance into value by offering one-to-one gifting, swag-select options and tracking benefits for businesses. Head of Sales Michael Goldenberg shares how he builds strategies tailored to individual challenges, below.    

 

What’s your blueprint for building a sales team?

When you’re building out a startup sales organization, you can most certainly try to avoid the mistakes and headaches you’ve seen created in other roles. But even that is a fool’s errand because you’re being led by biases of previous experiences instead of the specific scenario at hand. Much like a tiger and turtle survive and thrive differently, so does each startup sales organization.

Building a startup sales team is more like cooking. There are certain principles of balance you can expand upon. In sales, you want to balance good hard-working people who have enough experience to succeed quickly with enough hunger to push hard. You want to build a process that guides but doesn’t restrict. You want to build a set of tools that empowers but doesn’t paralyze. And perhaps most importantly, you want to build a culture of high performance that doesn’t burn out the people you depend on most.

 

How did you identify these keys and how have they made an impact as you build a team?

I identified most of these things while watching other people try to take their previous successes in other companies and industries and run that same playbook in an entirely different circumstance. I also learned many of these lessons from messing up myself, often trying tactics I took from other people only to find out they didn’t apply to my scenario. 

 

"Don’t assume what has gotten you to the top of the hill is enough to get you to the top of the mountain.’’

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

Once you have that fire started, keep adding to it. Don’t settle for the logs that are already there. That means doubling down on your efforts to hire, train, support and continue to maintain performance. Continue to emphasize the need for the team to continue to evolve and improve. Don’t assume what has gotten you to the top of the hill is enough to get you to the top of the mountain.

Build a strong foundation of people and culture so those employees have a stake in cultivating and shaping the future hiring and team enablement.

 

When a sales team meets its goals, a fancy dinner is a great way to celebrate: Time to make a reservation.

OpenTable, an online provider of restaurant reservations, has seated over 1 billion diners. Inside Sales Manager Jon Schwartz told us that hiring people who not only complement the company culture, but drive it forward, is a key driver of success.

 

 

What’s your blueprint for building a sales team? 

One of the best pieces of advice I got as a new manager was to first identify the attributes you can coach and then find the items that are less tangible but are core pillars to performance. With that in mind, I look for self-starters. Sales incentives and commission plans are great motivators, but my best reps all share the common trait of simply wanting to be successful and have a willingness to do more to exceed their targets. 

Second to intrinsic motivation comes problem-solving and critical thinking. It is difficult to coach people to be curious or to approach challenges with a solution-first mentality. At its core, sales is about identifying a problem and working with your customer to find the best solution for them. By staffing with those principles in mind, I can be confident they will take their personal goals and reverse engineer the work required to achieve them. They will navigate changes in product, pricing and availability with a solutions-driven mentality and help provide stability to an industry that is fast moving on a slow day. 

"Work with your team to add complementary people...” 

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

We first make sure we identify the characteristics of our best sellers, then we candidly communicate that to our recruiting and training team. As your department scales, time becomes increasingly scarce so having a recruiter shadow your sales team can help find new talent efficiently and seamlessly. 

Work with your team to add complementary people: do we want someone with tenure, high energy or strong leadership traits?

When it comes to finding a culture fit, consider what your current environment is and whether the person can maintain your culture, as well as add something to the puzzle and drive it forward.  Lean on senior sellers to assist with tasks like training, interviewing and team events since this will not only help their professional development and buy-in but also create another champion for the culture you want to uphold. 

 

Orel Levit, director of sales at vCita, is all about structure. Before he told his team what to expect from him, he mapped out leadership qualities that he expects from himself. And it’s clear where that structure and hard work fits into the business management and client engagement app, from the scheduling software feature to the online payment portal. 

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

When building a sales team, it’s important to understand what sales methodology is right for the type of customers you’re facing and the product you’re selling. Once I figured that out, I chose four values for myself and my team to follow: hard work, believing in yourself, proportion and appreciation. These four values create two pillars: momentum and resilience. 

Working hard and believing in yourself and in your team creates momentum. Putting your successes and failures into proportion and appreciating the opportunities you get every day creates resilience. Being resilient and keeping the momentum going has led to our success.

"Your leading representative shouldn’t always be your first pick to become a manager.’’ 

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place? 

This might be the hardest part about growing your sales team. Your highest priority is making sure you promote the right people to sales management. Your leading representative shouldn’t always be your first pick to become a manager. Choose the person who isn’t focusing only on their individual success but also helps the rest of the team while performing at a high level.

Once you have a quality leader, focus on training. Have weekly group meetings and one-on-ones to go over objection handling, pitches and call structure. But make it scalable. We created an online sales playbook available for the team that we update weekly.

 

As the VP of Sales at Chowly, which integrates third-party delivery platforms with restaurants, Tom Lawton does his best to pay attention to his individual team members. This means understanding understanding what motivates them — individually and collectively — as well as hearing what changes they’d like to see to sales protocols.

 

What’s your blueprint for building a sales team? How did you identify these keys and how have they made an impact as you build a team?

While I don’t believe there is a cookie-cutter blueprint to building and scaling a successful sales team, I do believe there are key factors to ensure the team has the opportunity to be successful. 

As a sales leader, creating a strong collaborative culture is the first thing I set out to do. You spend more time during the week at work with your team than you do with family and I am very intentional in building a team environment that supports that. After building that cultural foundation, you learn what motivates individuals and teams, so you can identify which levers to pull in certain situations. This could mean additional bonus incentives for a given time period, or collaborating with marketing on a specific message we want to spread to drive additional leads. 

Next, I really drive home understanding the science and art of sales, like knowing how many touch points, conversations and scheduled pitches it takes to close. Combining that with what you say, how you say it and your mindset throughout the entire sales process brings the formula of the science plus art to life.

 

I believe that while hiring is very critical, retaining your sales reps is even more important.”

 

When scaling, how do you ensure your team doesn’t lose the elements that made it so successful in the first place?

I believe that your team carries the culture as you scale. Ensuring that you never stop learning and continue to take in as much feedback from your team as possible as you scale is important. Every time we onboard someone, we ask for as much feedback as possible to ensure the next time, we get better as a leadership team. 

I want to ensure everyone has a voice as we grow. We hold quarterly meetings on any “sales-bible rule” changes the team would like to vote on. We create certain criteria but ultimately, the team adjusts the "settings" so we have 100 percent buy-in and alignment across the organization. 

While hiring is very critical, retaining your sales reps is even more important. From managers and directors to VPs, I want to make sure that when we hire someone, we give them every possible chance to succeed.