Jillian Basile believes that the best enterprise sales professionals act like the CEOs of their own businesses.
“They don’t just sell; they orchestrate outcomes,” she said.
As director of enterprise sales at Jasper, Basile strives to empower her team to orchestrate meaningful outcomes, serving as a “coach and force multiplier.” She focuses heavily on education, translating market shifts and customer feedback into practical insights to help those on her team effectively handle both viable opportunities and at-risk deals.
“These insights drive cross-functional alignment, which is critical in the best enterprise organizations,” Basile said.
Collaboration is key in enterprise sales, which is something that Monica Pasadas has learned firsthand as a senior enterprise account executive at Zocdoc. She spends her workdays checking in with a variety of stakeholders to discuss performance trends and share insights, guided by the belief that her role, at its core, is to be a trusted advisor to both teammates and the company’s customers.
“It’s a mix of relationship-building, problem-solving and execution — all in service of creating impact,” Pasadas said.
For Basile, Pasadas and 10 other professionals from companies like Motorola Solutions and Spectrum, working on their teams offers the opportunity to pursue a dynamic career while driving change for others in the process. Read on to see what each individual had to say about their career journeys, how they broke into enterprise sales and what others can do to follow in their footsteps.
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Motorola Solutions builds safety and security solutions that protect people, property and places.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
As a senior sales director, I lead a team of 25 people to drive strategy and planning for a territory that spans 13 states. My regional sales directors and I are driven by one thing: listening to our customers and understanding their business needs. Our customer engagement and solutions planning, from roadshows to our internal product and implementation meetings, is designed to ensure customers have a white glove experience that prioritizes their needs.
A central part of this is about simplifying our customers’ buying experience. We know that enterprise sales can have long cycles and multiple decision-makers, making it complex for any organization to manage. My job is to equip our sellers with the right tools, from detailed insights on customers’ requirements to alignment with the right inside sales partner for their territory. This allows my team to serve as valuable guides to customers through their buying journey, ensuring relevant and productive conversations. A precise strategy is built around each customer, aligning them with the best experts and the right solutions for their operations.
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
My break into this market wasn’t a single moment but the result of getting in with a growing company and building on my experience to tackle larger, more complex opportunities over the years. I started my career working for an Avigilon channel partner, which provides video security and access control solutions. In this role, I gained experience working on medium-sized enterprise deals, providing the critical experience to join Avigilon in 2012.
Avigilon provided invaluable exposure to true enterprise sales. At the time, the company was smaller, but as we brought on larger accounts, we grew organically into the enterprise space. Eventually, we were acquired by Motorola Solutions in 2018, and I’ve been with the company ever since. It’s a great place to work because they provide me with support and opportunities to grow.
As a manager, I’m enthusiastic about bringing new talent into the company. When you’ve got good people around you, exciting initiatives and exceptional technologies, it’s easy to continue being passionate and growing professionally. I love helping people, and addressing our customers’ safety, security and operational challenges is incredibly rewarding.
“I love helping people, and addressing our customers’ safety, security and operational challenges is incredibly rewarding.”
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
Start with an unequivocal passion for the customer. Be curious and fearless. Have a genuine willingness to learn about the products and why they matter to a customer. Don’t be intimidated by the idea of calling a large enterprise customer. What’s great about Motorola Solutions is that you have an expert support system to help you succeed.
What makes a sales rep stand out is a combination of creativity, collaboration and persistence. In sales, you’ll hear “no” far more than “yes,” so you have to be resilient and willing to pick up the phone. It’s about recognizing a customer’s needs and demonstrating in a compelling way how our technology can be the solution.
Finally, I highly value professionalism and follow-up. These traits build strong, lasting relationships. A standout rep is proactively engaged with the key decision-makers, following up to ensure they have the information they need, answering questions quickly and doing all you can to support their needs.
Curiosity gets you in the door, persistence keeps you in the game and professionalism builds trust. Master that combination, and you won’t just stand out — you’ll become invaluable to both your customer and your company.
Spectrum is a connectivity company that provides internet, mobile, video and voice services across 41 U.S. states.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
As a business development manager at Spectrum Business, I lead a team of nine BDRs. We support our assigned sales teams as dedicated prospectors, identifying potential challenges our customers face and setting up discovery meetings so that our sales team can drive new business. Day to day, I’m coaching BDRs to drive effective, strategic outbound prospecting, ensuring they have the support they need to succeed and that we are contributing to the company’s growth.
“Day to day, I’m coaching BDRs to drive effective, strategic outbound prospecting, ensuring they have the support they need to succeed and that we are contributing to the company’s growth.”
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
My tendency to let curiosity be my compass is largely what brought me to telecom. I’m always looking for ways to use my creative energy. When it comes to my team prospecting for new business with large, Fortune 500 companies, it’s exciting to help BDRs explore and find ways to crack the code on clients’ business needs. By identifying the products and services our sales teams can offer them, we act as the spark to a symbiotic business relationship.
My path into sales wasn’t traditional; I didn’t have direct sales experience. I was fortunate to be selected to participate in Spectrum Business’ inaugural Business Development Campus Hire Program. The Spectrum Business Development team was piloting a three-month program focused on sales and prospecting, while also developing emotional intelligence and a growth mindset. That program became the launchpad for my journey, starting as a BDR 1 before advancing through to BDR 2 and BDR 3.
Along the way, the leaders I’ve had at Spectrum set a standard for me to aspire to. Now, as a new people leader, I get to help my team grow based on the leaders I’ve learned from throughout my career.
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
My advice to anyone interested in a career in sales is to start developing your skills. Learn how to communicate effectively, build your professional network and learn to listen more than you speak. Following a process or playbook and hitting your targets will make you a good rep, but taking the initiative to do what’s right for the customer, genuinely help them and exceed their expectations is what takes you from a good rep to a great rep.
Datadog’s platform enables digital transformation, cloud migration and infrastructure monitoring of teams’ entire technology stacks.
Tell us about your career journey so far.
My career in sales started at IBM, where I learned the fundamentals and saw firsthand what great sales execution looks like, a foundation that’s guided every step of my journey in sales. After several years in sales, I had the opportunity to step into leadership, a shift that gave me a whole new perspective on what success looks like. I discovered how rewarding it is to help others grow, celebrating their wins and seeing their development translate into customer success. That experience showed me that leadership is really about multiplying impact driving transformation not just for customers but for the people you work alongside every day.
That’s what led me to Datadog — the opportunity to continue growing as a leader and to help customers harness the power of a platform that drives innovation across their entire business. It’s an exciting time to be part of Datadog’s enterprise sales organization. The growth, the scale and the chance to partner with global customers make it an incredible place to build and grow your career. Datadog’s culture values ownership, trust and collaboration, the same principles that have guided how I lead teams and build lasting customer relationships.
Why did you choose a career in enterprise sales?
What first drew me to enterprise sales was the chance to work at the intersection of people, technology and transformation. Every engagement is an opportunity to help organizations tackle meaningful challenges and help them differentiate and excel in their markets. That’s what makes Datadog such an exciting place to be, as the platform touches every part of a customer’s business, creating opportunities to drive real outcomes at scale. It’s a career that challenges me to stay curious and keep learning as new technologies reshape the way businesses operate. For me, there’s nothing more fulfilling than partnering with organizations and helping them unlock what’s possible through technology.
“Every engagement is an opportunity to help organizations tackle meaningful challenges and help them differentiate and excel in their markets.”
In your opinion, what qualities define a successful enterprise seller? What advice would you give to someone looking to build a career in enterprise sales?
What sets great enterprise sellers apart is their unapologetic curiosity. They seek to understand how businesses work, what challenges leaders are facing and how technology can open new opportunities for growth. They’re problem-solvers and innovators who aren’t afraid to think big or challenge the status quo. This role also takes real technical horsepower; you have to be able to translate complex technology into clear, actionable value for your customers. And none of it happens alone. The best outcomes come from collaboration, both across your own organization and with your customers. At its core, enterprise selling is about being a strategic advisor helping organizations modernize legacy processes, navigate change and build something better than what existed before.
For anyone looking to build a career in enterprise sales, I’d say start by mastering the fundamentals. Learn how to ask great questions, understand your customers’ world and seek out mentors who can help you grow and learn. I’ve found that Datadog is the perfect place to do exactly that, offering a culture built on trust, curiosity and ownership that empowers sellers to lead with customer obsession, think creatively and stay relentlessly focused on delivering value to customers.
TransUnion is a global information and insights company that aims to help organizations understand consumers more effectively and deliver personalized experiences.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
I serve as director of sales, leading three frontline managers who run our small- and medium-sized businesses TruLookup account management and business development teams. The client value executive team is responsible for roughly 20,000 accounts across our book of business. Day to day, the managers handle the majority of escalated calls, coaching, pipeline and on-on-ones; what escalates to me are the complex situations and strategic decisions that require a longer‑range view. We’re typically working six to twelve months out to ensure we’re operating effectively and efficiently.
New business development representatives focus first on high‑quality qualification, especially on inbound leads and prospecting. Our teams primarily sell an investigative data platform used for locating individuals across several key markets. Because of the sensitive nature of the data, every prospect goes through a strict credentialing process, and we enforce strict permissible‑use standards. I sit on a weekly corporate investigations committee that reviews misuse and, when necessary, terminates access, staying aligned with frameworks like Fair Credit Reporting Act and the Driver’s Privacy Protect.
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
I’ve spent my career in sales, but I actually started by trying to become a software developer. A mentor quickly helped me realize my strengths were elsewhere and suggested I try selling the software instead. That pivot clicked. Early on, I sold into the public sector, particularly county governments and clerks of court, which taught me relationship‑building and consultative selling in complex buying environments.
From there, I moved into startups and enterprise software/SaaS, including big data and compliance domains. One formative chapter was in anti‑money‑laundering solutions, where I resold a major third‑party data set across financial institutions, spending time in the Caribbean, where anti-money laundering risk is heightened. That experience made the transition to my current data‑driven role feel natural.
What kept me in enterprise sales was the combination of people, problem‑solving and ownership over outcomes mentality. I still remember closing a six‑figure enterprise deal with a large healthcare entity entirely over the phone, which reinforced how trust and value creation, not just geography, win. Over time, I began building teams, and when I joined TransUnion, I was drawn to the leadership vision, people‑first culture and the balanced, high‑performance environment, now operating in a hybrid model that leverages focused in‑office collaboration.
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
First, be curious and be hungry. Curiosity fuels the questions that uncover problems worth solving; hunger gives you the resilience to push through the many “nos” on the way to “yes.” Enterprise selling rewards people who are coachable, organized and eager to learn, especially early‑career sellers. That’s why we recruit from programs that actually teach sales as a discipline; the structure and habits show up quickly on the job.
“Curiosity fuels the questions that uncover problems worth solving; hunger gives you the resilience to push through the many ‘nos’ on the way to ‘yes.’”
As for what separates great from good: A good rep can fulfill a stated need, while a great rep can create the need by asking smart, open‑ended questions that surface latent pain or opportunity the buyer hadn’t fully articulated. The best enterprise sellers are consultative, relationship‑driven and intentional about “making friends” — building trust and likeability while guiding customers through a solution. They weave in relevant cross‑sell questions without sounding scripted, and they keep going when the day’s tally is heavy on “nos.” People buy from people they like and people they trust, and that won’t change.
Zocdoc’s platform enables people to book appointments with nearby in-network physicians.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
In enterprise sales, every day is about balancing strategy and execution. I manage a multi-million-dollar book of business, helping clients grow while driving measurable outcomes. My work spans strategic account planning, forecasting and using data to uncover opportunities that improve performance in measurable ways that naturally unlock client growth.
I spend my days connecting with a variety of stakeholders, discussing performance trends, sharing insights and collaborating across teams to deliver results. At its core, this role is about being a trusted advisor: aligning solutions to client goals, ensuring accountability and finding smart ways to grow together. It’s a mix of relationship-building, problem-solving and execution — all in service of creating impact. In enterprise sales, no two days or clients are the same. Pairing this with an impactful mission — to give power to the patient — makes my role at Zocdoc interesting and rewarding.
“It’s a mix of relationship-building, problem-solving and execution — all in service of creating impact.”
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
My path in sales has been fairly traditional, starting in local, moving to mid-market and now thriving in enterprise. I began in a classic small to medium-sized business role where I learned the fundamentals: how to really listen, understand a client’s problem and offer a solution that truly fits. From there, I moved into mid-market sales, where the challenges grew into larger budgets, stricter key performance indicators and multiple decision-makers came into play.
That experience taught me to think strategically and work backward from a client’s goals. Now, in enterprise, it’s all of that magnified. The problems are more complex, the collaboration is deeper and the impact is even greater. What’s stayed constant through it all is what I love most: partnering with clients to unlock growth and build something meaningful together.
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
If you’re curious about breaking into enterprise sales, my best advice is to turn that curiosity into everyday actions. Enterprise sales isn’t about chasing quick wins; it’s about building partnerships that last. Get to know your clients deeply regarding their goals, challenges and how they operate. The better you understand them, the easier it is to spot new ways to help them win.
Focus on conversations that deliver real value and naturally open doors for growth. Partner closely with customer success and product teams to make life easier for your clients. Stay sharp on trends, look for expansion opportunities and catch red flags early.
You’ll stand out by being reliable, adaptable and bringing smart ideas to the table. Shadow great reps, get comfortable talking to executives and learn from leaders who’ve navigated large organizations before. At the end of the day, the best reps meet clients where they are, because strategies evolve, and agility is everything.
Dandy develops devices and software-based solutions for the dental industry.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
I lead enterprise sales at Dandy, partnering with large dental support organizations to modernize treatment. My role blends strategy and execution — building the team, refining our go-to-market playbook and working closely with engineering and product to ensure we’re solving the right problems for customers. Day to day, that means anything from hands-on deal work to long-term planning that evolves a dozen times before it becomes reality.
“My role blends strategy and execution — building the team, refining our go-to-market playbook and working closely with engineering and product to ensure we’re solving the right problems for customers.”
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
I started in technical roles in software development. By chance, I ended up helping on the business side of a deal with a surgical robotics company. I loved the challenge of aligning so many different teams toward a shared goal and seeing progress that came directly from my work. That experience pulled me into enterprise sales full time, where I found my passion — combining technical problem-solving with storytelling, strategy and building partnerships.
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
Focus on learning. Find mentors you respect, ask as many questions as they’ll entertain, and read constantly. Breaking in comes down to finding great companies and reaching out with intention; someone will give you a shot. Once you’re in, get as many hard reps as possible. You learn the most when deals stall, negotiations drag or customers walk away. The people who stand out are the ones who listen, stay calm under pressure and make it easy for others to trust them.
Jasper’s marketing solutions are designed to help marketers automate and accelerate processes, collaborate on projects and more.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
My role is to act as a coach and force multiplier. My meetings can range from game-planning a C-level meeting to navigating a tough procurement negotiation. We review the value hypothesis, map key players and strategize on achieving executive alignment. It changes every day, which is part of the fun.
A big part of my role is education. I translate market shifts and customer feedback into practical insights for our teams and help customers define and reach their best outcomes. Jasper encourages self-starters and looks for people who seek out learning and go out of their way to understand both our technology and our customers’ worlds. With so many competing priorities, I need to understand which deals are viable, which are at risk and what strategic levers we can pull. These insights drive cross-functional alignment, which is critical in the best enterprise organizations.
My responsibility is to foster a healthy and innovative culture for my team to thrive. This means creating an environment of high accountability but low ego, where people are obsessed with our customers’ success. At Jasper, we look for people who find energy in shaping the future of an evolving industry.
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
For nearly a decade, I was part of Flight Centre Travel Group, where I learned how to navigate the complex needs of large clients and internal teams. That experience sparked my interest in enterprise sales and taught me the importance of strategic thinking, research and teamwork. I progressed from an individual contributor to vice president and helped scale our division from $50 million to $250 million in revenue, an experience that shaped how I lead and collaborate today.
Five years ago, I transitioned into tech to take on new challenges. Since then, I’ve worked with organizations like Boeing, Sanofi and Nasdaq, helping them address complex issues across talent and go-to-market strategy. That work gave me a front-row seat to how technology and AI are transforming entire industries, a shift that makes our mission at Jasper especially exciting.
Sales is a unique career in that it allows professionals to move fluidly between individual and leadership roles, adapting to different stages of life. I’ve recently returned to people management, where I can help others grow and succeed.
“Sales is a unique career in that it allows professionals to move fluidly between individual and leadership roles, adapting to different stages of life.”
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
Top-performing enterprise representatives act like CEOs of their own business. They don’t just sell; they orchestrate outcomes. Their success comes from deeply understanding customer needs and turning those insights into business cases that deliver both immediate and lasting value. Instead of focusing on product features, they demonstrate real business acumen, speaking the customer’s language around budgets, priorities and impact.
Great sellers combine executive presence with strong relationship-building. They know how to build a coalition of support inside the organization, staying connected with champions and executive sponsors alike. With consistent discipline, they manage their business with the operational rigor that builds trust and drives results.
What sets a Jasper seller apart is curiosity and drive. They’re self-starters who seek context, stay plugged into AI and market trends, and thrive in a fast-moving environment where the playbook is still being written. The people who excel here are energized by change and see every deal as a chance to build something new.
Riskified’s AI-powered platform is designed to help e-commerce brands protect themselves against chargebacks, mitigate fraud and policy abuse, and improve customer retention.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
As director of business development at Riskified, my team’s goal is to initiate conversations with companies experiencing issues with online fraud and abuse that impact their growth. To achieve this, each BD must become an expert in our product, our industry and how Riskified enables exceptional outcomes for our merchants.
Our short-term work involves organized daily activities, including researching companies, prospecting potential buyers and drafting compelling visions of how Riskified can help them achieve their goals. This is typically done via email, LinkedIn or pitched live during a call. Our long-term work involves weekly training sessions on topics ranging from best practices for merchant calls to the technical capabilities of our AI/ML engine. Working collaboratively and prompting the team to share ideas and tactics helps elevate our winning strategies.
My responsibilities include keeping the team on task and focused on these challenges. It’s always rewarding when we work together to achieve success for our merchants.
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
I started my professional career in business development after graduating from college. At the time, I was following advice that, as a competitive, team-driven person who enjoys learning and taking feedback, sales could be a great fit and would afford me multiple paths for professional growth. That advice turned out to be true.
I was fortunate to gain experience working at smaller startups that were looking to find their market fit, which immediately provided me with a testing ground to hone my skills in the fundamentals of software sales. Understanding how to prospect effectively and hold conversations with buyers came through trial and error but even more so from learning from managers and mentors. As my skills improved over time, I transitioned into sales leadership, where I have helped new salespeople achieve success in contributing to the business and our merchants’ overall goals.
At Riskified, the opportunity to sell into an enterprise market has been a truly awesome challenge. I believe that sales is part art and part science. With enterprise sales cycles, you need to use both, as well as strategy, patience and teamwork, which never leads to a dull day.
“I believe that sales is part art and part science. With enterprise sales cycles, you need to use both, as well as strategy, patience and teamwork, which never leads to a dull day.”
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
At its core, enterprise sales is about solving problems for businesses. There are numerous ways to solve problems, and the world of software sales is full of companies vying to perfect their strategy. Taking that into account, my advice is straightforward: Conduct as much research as possible, and seek advice from as many people as possible. In doing that, if you find that solving business problems interests you and the prospect of owning your own book of business excites you about the future, then enterprise sales could be a good fit for you.
That’s the advice I’d give an aspiring salesperson, as it mirrors the biggest drivers of success in the role. You will need to be a high-level expert, an evangelist willing to speak to multiple prospects at a moment’s notice and enthusiastic in the face of adversity. It’s not easy, but it’s a role where every day brings new challenges and opportunities for growth.
Lessen aims to make it easier to care for and improve real estate properties, offering a platform that provides data-driven insights for investors, owners, managers and service providers.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
As an enterprise sales director in Lessen’s commercial division, my focus is on helping large, multi-site property owners and operators modernize how they manage their facilities. Every day is a mix of strategic calls with executives, discovery sessions to uncover inefficiencies and collaboration with our internal teams to design scalable solutions. I spend a lot of time understanding clients’ operational realities: how they manage maintenance, vendor networks and budgets, and aligning our technology to streamline those workflows. It’s part sales, part consulting and part long-term partnership-building. At the enterprise level, success isn’t about closing quickly; it’s about creating meaningful, measurable impact for the client.
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
My path into enterprise sales started with curiosity. I’ve always been fascinated by how large organizations operate and the challenges that come with scale. Over 15 years in sales and business development, I’ve worked across commercial real estate, facilities management and tech-enabled services. Early on, I learned that selling to enterprises requires more than a great product. It takes empathy, data and a deep understanding of the customer’s world. I was drawn to that complexity. Each deal is like solving a puzzle, and the reward is seeing your solution improve performance across hundreds or thousands of locations. That’s what keeps me motivated.
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
Start by mastering the basics: listening, discovery and storytelling. Enterprise sales isn’t about volume; it’s about value. You need to think like a consultant, not just a seller. Learn your clients’ industries, understand how they make money and speak their language. Build relationships that outlast individual deals. The best enterprise reps don’t chase transactions; they build trust and deliver insights that help clients see around corners. And don’t rush the process. Enterprise sales cycles can be long, but if you stay consistent, keep learning and show up with genuine curiosity, you’ll earn a seat at the table.
Consumers use Trustpilot’s platform to write reviews about a wide range of businesses, from banks to clothing retailers.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
As an account executive, the best days are made up of talking to customers and prospects and learning about their day-to-day challenges and opportunities. Outside of that, it’s researching what I can about a company to try and put myself in their shoes and presenting valuable solutions for them. You don’t always get it right, and you’ll always need their context. But when being genuinely curious about a company and contact is how you spend your time, your positive intention to help them is clear.
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
I started, like many, in a sales assistant/account development representative type role. I went where the AEs needed me. As I learned more, I was always drawn to more complex businesses with global focus and the biggest opportunities — but also the biggest risks.
I found the most joy in learning, which continued as I pivoted to an enterprise AE then an enterprise sales manager role. Learning about the day-to-day work of prospects at these big companies and areas where they could see efficiencies, process improvements and valuable partnerships to best serve their customers was always the most compelling part for me. I surrounded myself with folks who excelled there and those customers. That, plus a mentor, John Kelly, were my “way in.”
This is still the case, even now as an end-to-end enterprise Leader. I love working with companies, teams and people who make it their mission to help other people solve problems, improve our customers’ day-to-day and deliver real business impact.
“I love working with companies, teams and people who make it their mission to help other people solve problems, improve our customers’ day-to-day and deliver real business impact.”
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
Listen more to prospects, and ask all the questions — yes, even to those contacts who may be reluctant to answer a salesperson. I have some advice for these people, too. More often than not, your salesperson really cares about helping you, so cut them some slack!
Get creative about helping them by putting yourself in their shoes. And believe it or not, if your solution can’t help them, tell them that, too! Even that is helpful.
Genuine curiosity is the key to not just enterprise sales success but also to developing your general business knowledge every single day. Stop thinking you have or are supposed to have all the answers; selling an enterprise buyer requires mutual learning and commitment to building a solution together. Get collaborating!
Templafy’s platform helps organizations reduce manual work by enabling them to automate business document creation.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
My business development role is all about communication, curiosity and attention to detail. I stay up to date on trends in marketing, digital transformation and AI to better understand how companies work, and I use those insights to create relevant outreach through calls, emails and social media. Sales is ultimately about human connection, and I find that empathy — with a touch of humor — always helps me break through the noise. LinkedIn is an essential tool for researching accounts, finding decision-makers and personalizing outreach. It’s also where I build awareness and promote our services by sharing regular posts about product updates and my own experiences to build credibility and connection.
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
I started my career as an executive assistant to C-level leaders at consulting and finance firms in Italy, my home country. That experience gave me a strong foundation for sales: It taught me how to communicate clearly, stay organized under pressure and understand how business decisions are made. After moving abroad from Ireland to the United States and working across different cultures and industries, I developed a natural ability to connect with people and adapt to new perspectives. Collaborating with great leaders along the way helped me grow both personally and professionally, shaping a strategic mindset that led me toward enterprise sales.
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
Breaking into enterprise sales takes patience and a real desire to learn. Focus on understanding how businesses work, namely their priorities, challenges and decision-making. Collaboration is key, so work closely with account executives, marketing and leadership across your organization to bring the right ideas forward. And above all, stay resilient — every “no” helps you learn. Never give up, and always turn rejection into a chance to understand what happened in that specific market so it can open the door to new opportunities.
Founded in 2010, commercetools is the company that made “headless commerce” mainstream, offering a platform that enables teams to build and scale e-commerce experiences at their own pace.
Tell us about your role in enterprise sales. What kinds of tasks, calls and other responsibilities do you tackle on a regular basis?
My activities are structured around long, strategic sales cycles versus high volume. I support a book of business of about 30 accounts, both current and prospective, and my role is to deeply understand their pain points and connect them to the solutions that commercetools sells. I do this through extensive research, from annual reports to financial analysis to news coverage.
This enables me to be a strategic partner. I use org chart mapping to identify key players, their influence and decision criteria, which I validate with tailored proposals. I then work with the customer and our value engineering team to build the business case and quantify their return on investment. A huge part of my day is building and strengthening relationships with customer teams and commercetools’ senior leadership, which is integral to the sales cycle.
Ultimately, I lead the sale and negotiation. I serve as the main point of contact for every phase, from initial discovery conversations using frameworks like the Metrics, Economic Buyer, Decision Criteria, Decision Process, Identify Pain and Champion framework to managing the support team, addressing deal blockers and negotiating pricing, contracts and service level agreements. The key to success here is knowing where the market is and being competitive.
Tell us about your professional background. What made you want to work in enterprise sales, and how did you break into selling for that market segment?
My background is in kinesiology. I was a competitive gymnast for most of my life, so I wanted to get into something that was centered around movement. However, once I graduated, I realized that this felt more like a passion project than a career. At the time, I saw a lot of my friends getting into tech. I didn’t really know much about the industry, but I was told over the years that I was good with people, which would make me good at sales. I knew I had a lot to learn, but I wanted to give it a shot.
I started as a BDR at a technology company, and I knew right away I wanted to go to the top of this profession. I saw how the relationships my colleagues were building were changing the very trajectory of the company. I wanted to work for companies that sold large infrastructures that would enable a full digital transformation versus a point solution — to become a strategic advisor to brands looking to make a change to their business and operational procedures. After years of working my way up through smaller deals and companies, I ended up in the enterprise space, selling to larger businesses with more complex challenges, and this is exactly where I’m meant to be.
What advice would you give a sales rep looking to break into enterprise sales? What makes a stand-out enterprise sales rep?
Don’t be afraid to do the dirty work and start at the entry level. I started as a BDR making cold calls, getting stood up for meetings and sending thousands of emails to never get a response. It was hard work, but it was the best way to learn.
“Don’t be afraid to do the dirty work and start at the entry level.”
Each level in sales builds on the other and teaches you something for the next opportunity. Don’t be afraid to make bold statements and action toward the path you think is right. If it’s wrong, you will learn and fix it the next time.
Last but not least, don’t ride the highs or the lows — stay in the middle. Sales is constantly changing internally and externally. Markets change dramatically, and you need to remain neutral so you don’t ride the roller coaster but rather remain focused on the long-term goal, which is ultimately serving the client and providing them with the best experience to evaluate if their software is a good fit for their business needs.
