What It’s Like to Build a Meaningful Sales Career at These 10 Companies

The most successful sales teams are fueled by two things: camaraderie and career growth. 

Sales is truly a team effort, driven by professionals who are eager to share strategies, cheer each other on and ensure everyone is aligned around common goals. 

That’s why unified payments and financial platform provider Airwallex’s sales team members work together all the time, even when they’re striving for individual career growth. According to Senior Sales Manager Cainen Gerety, the company supports sales team members in different ways, such as skill-building sessions, mentorship and AI-enabled resources that help reduce administrative work. 

“The goal is simple: Give you the context, coaching and practice to do good work, then keep getting better at it,” Gerety said.

Director of Sales Chris Douglass said that his employer, AI work platform provider monday.com, takes a similar approach to helping sales team members succeed. The company offers formal initiatives such as weekly training sessions and a newly launched career framework, which allows reps to rate themselves across five criteria, both at their current level and the level they’re aiming for, so they know how to progress. 

“We celebrate the wins, learn from the losses and push one another to get better,” Douglass said.

Below, Gerety, Douglass and sales leaders from eight other companies share what it’s like to grow on their teams while driving business success. 

 

Airwallex is a fintech company offering a unified payments and financial platform that helps organizations manage business accounts, payments, spend management and embedded finance.

 

What’s it like to work on the sales team at Airwallex?

On Airwallex’s U.S. SME and growth team, I help cross-border companies eliminate financial friction across payments, global accounts and spend. You’re expected to deeply understand how businesses operate and partner with product, operations, risk and tech to build practical solutions. We don’t just put a software dashboard on top of old bank technology. We built the actual global financial infrastructure, the underlying plumbing, from scratch. Owning this core engine lets us solve complex cross-border bottlenecks for scaling SaaS, travel and service businesses without the delays of traditional banks. You aren’t handed a rigid script. Account executives have the authority to write regional playbooks, shape territory strategies and test what works. You get the pace of an emerging market, backed by a product serving 600,000+ companies globally. Success here is a team effort. You’ll learn quickly by staying close to the deal and the customer. Peers help you sharpen your judgment, ensuring the solution works long beyond the close. At the forefront of fintech and AI, we offer real velocity, room to grow and competitive compensation for builders who own their outcomes.

 

“At the forefront of fintech and AI, we offer real velocity, room to grow and competitive compensation for builders who own their outcomes.”

 

What does career growth look like for sales employees on your team?

Career growth here is tied to the impact you have and the ownership you take. For high performers, moving into leadership or a senior individual-contributor role is one of the routes you can take. SDRs can move into AE or CSM roles, while SME and startup AEs can take on mid-market and enterprise work. AEs can also move into account management or partnerships.

Growth is about more than a title. As your scope grows, so does the complexity of the work. Senior sellers partner with solution engineers on technical opportunities, including API integrations, to make sure customers are set up for success. They can also build playbooks, lead strategic projects and develop expertise in a vertical such as e-commerce or travel.

We support that progression with regular one-on-ones, skill-building sessions and mentorship from experienced sellers and leaders. You’ll get practical feedback on live opportunities and work with your manager to map the skills and experience needed for your next move. The path won’t look the same for everyone, but strong performance and ownership can open new opportunities.

 

What training, coaching or resources help sales employees succeed and advance?

We move quickly, but we don’t leave you to figure everything out alone. Onboarding starts with structured training led by our local enablement team. You’ll learn who we serve, how our products solve customer problems and the prospecting motions that work. You’ll work through real case studies, complete relevant product training and have an onboarding buddy to help you get up to speed.

The support continues once onboarding ends. Team enablement sessions cover practical sales skills and product updates, while regular one-on-ones with your manager focus on the opportunities in front of you and the skills you want to build. Managers also work alongside sellers on early and complex opportunities, so coaching is tied to real customer conversations.

You’ll also have access to sales tools and AI-enabled resources that help reduce administrative work and keep more time focused on customers. Quarterly commercial kickoffs bring the team together for hands-on workshops, product training and time to learn from one another. The goal is simple: Give you the context, coaching and practice to do good work, then keep getting better at it.

 

 

 

Datadog’s AI-powered monitoring and security platform enables digital transformation, cloud migration and infrastructure monitoring across companies’ technology stacks.

 

What’s it like to work on the sales team at Datadog?

Sales at Datadog is fast-paced, highly engaging and extremely relevant, as Datadog lives ahead of most emerging trends, whether it was the shift to cloud or today’s AI era. The sales organization is very new logo-focused to bring in new revenue while doing transformational expansions with current customers. Focus for sales teams is finding the most impactful problems and solving them based on high value returns for both technical and business functions. The platform is broad, and while we continue to venture into new use cases, the existing offering continues to be more comprehensive and allows customers to truly consolidate and leverage Datadog as the control plane for building software, ensuring reliability and leveraging AI to make teams more productive.

 

“Focus for sales teams is finding the most impactful problems and solving them based on high value returns for both technical and business functions.” 

 

What does career growth look like for sales employees on your team?

Datadog has a very defined career pathing guide for employees in all roles. On the sales side, career progression forks into two paths with significant runway in both lanes.

Individual contributor: Enterprise account executives who prove themselves on both new logo acquisition and large transformational deals grounded in value get promoted to strategic AE then senior strategic and can continue growing with their customers to major AE and senior major AE

Leadership: AEs who engrain themselves in the playbook and can not only follow the playbook but continue to make improvements often move up to leadership roles. Frontline leadership at Datadog is predominantly internal promotions with people who love to build and drive success for others by teaching in the field. Director of enterprise sales -> senior director -> regional VP is the defined plan and we have multiple individuals who have moved up three to four levels based on meritocracy and impact to the region.

 

Employees can partner with Garner Health to offer a benefit program that helps employees find doctors in their local communities. 

 

What’s it like to work on the sales team at Garner Health?

It’s a high-performing sales team with a little bit of nerdiness mixed in. We’re obviously responsible for helping prospects understand Garner and ultimately buy into the program, but there’s also a very analytical side to the job: reviewing plan designs, handling renewals and claims data, and figuring out how Garner fits strategically. You have to know your stuff to be successful here. At the same time, it’s the most supportive sales team I’ve ever been part of. People share ideas, help each other solve problems and genuinely want the person next to them to win.

 

“People share ideas, help each other solve problems and genuinely want the person next to them to win.”

 

What does career growth look like for sales employees on your team?

One thing I’ve come to appreciate more and more is how many different ways there are to grow at Garner. There’s a path to level up whether you want to become a more senior individual contributor, work on larger strategic opportunities and mentor others, or eventually move into leadership. And because the company is growing so quickly, those opportunities naturally continue to present themselves.

 

What training, coaching or resources help sales employees succeed and advance?

Garner invests a lot in making sure people are set up to succeed from day one. Onboarding is very structured. You spend time learning the product and the industry, practicing your pitch and getting feedback from the team before you ever hit the market. That coaching continues once you’re in the role, both one on one with your manager and through broader team forums, and senior people are always willing to jump in and help.

We also have a really strong set of tools, and I especially appreciate how much Garner has embraced AI. People are encouraged to experiment with it, share what’s working and learn from each other, which has helped us find better ways to work and given the team a real productivity edge.

 

 

HiBob’s HR platform helps HR teams and managers handle onboarding, compensation, surveys, employee performance and other tasks. 

 

What’s it like to work on the sales team at HiBob?

Working on the sales team at HiBob is high-energy, collaborative and very growth-oriented. It’s an environment where people are expected to take ownership, move with urgency and continuously improve, but they’re also supported by a team that wants to see them succeed.

We believe the best sales teams win together. BDRs/SDRs, AEs/AAEs, managers, enablement, marketing and RevOps work closely together, and there’s a strong emphasis on transparency, feedback and sharing what’s working and what needs refinement. It’s a performance-driven environment, but it’s also one where people are encouraged to bring their own perspective, ask questions and learn from each other.

 

What does career growth look like for sales employees on your team?

Career growth at HiBob is not limited to moving into the next title. It starts with building strong fundamentals, developing new skills and taking on more ownership over time.

For BDRs/SDRs, that can mean progressing into more senior roles, moving into AE positions or growing into leadership and other GTM functions. We also encourage people to identify the skills they want to build and look for opportunities to stretch beyond their current role.

One of the biggest things we look for is a growth mindset. Strong performance matters, but so does how you respond to feedback and how consistently you challenge yourself to get better.

 

“Strong performance matters, but so does how you respond to feedback and how consistently you challenge yourself to get better.”

 

What training, coaching or resources help sales employees succeed and advance?

We put a lot of emphasis on coaching because we believe people develop fastest when they have consistent feedback and a clear understanding of what great looks like. That includes structured onboarding, ongoing enablement, manager coaching, role plays, call reviews and regular performance conversations.

Just as importantly, we create an environment where feedback happens continuously, not just during review cycles (which we call “HiGrowth”) or only in one-on-ones. The goal is to give people the clarity, resources and coaching they need to perform in their current role while also building the skills required for their next one.

 

 

Founded in 2012, monday.com is an AI-powered work platform that empowers teams to orchestrate complex workflows, automate manual tasks and execute their work.

 

What’s it like to work on the sales team at monday.com?

One of the things I hear most often from the team is that this is a team that genuinely wants to win together. We sell solutions that work. Our sellers get to work directly with business owners and leaders every day, and as a leader, it’s incredibly rewarding to watch our team listen to a customer’s challenges, uncover what they really need and connect those needs to what monday.com can provide.

We also move fast and think entrepreneurially. Every day is different, from discovery calls and demos to pricing and negotiations, while learning to navigate different industries and business challenges. As a sales director, I love seeing people grow in that environment and become more confident, strategic sellers.

Most importantly, our team is highly collaborative. We share ideas, messaging and lessons learned, and people genuinely want to see each other succeed. We celebrate the wins, learn from the losses and push one another to get better.

Our customers love monday.com, and we love selling it. Great solutions, ambitious goals, a team that wants to win and a culture where people support each other — that’s what makes working here so exciting.

 

“Great solutions, ambitious goals, a team that wants to win and a culture where people support each other — that’s what makes working here so exciting.”

 

What does career growth look like for sales employees on your team?

There is a tremendous amount of opportunity for career growth on our sales team, both within the role and across the business. My goal is to foster an environment where reps keep expanding their skills and build a career that matches their ambitions.

Growth doesn’t always mean management. Reps grow within their role by taking on bigger, complex customers, selling from small businesses through enterprise and becoming more strategic sellers. Because our team isn’t heavily segmented, reps work across company sizes, industries and motions, a broader skill set than a specialized team offers.

There’s also real mobility. We’ve seen reps move between AE and AM, and from sales into product and enablement. For those interested in leadership, there’s a clear path from an individual contributor role into management. My philosophy: If someone raises their hand and shows ambition to grow, we will invest in them with bigger opportunities, leadership exposure —  whatever it takes.

monday.com is also a company where the pace of innovation, especially in AI, keeps creating new career paths. You have to raise your hand, and as a leader, my job is helping you build the skills to take that next step.

 

What training, coaching or resources help sales employees succeed and advance?

One of the things that stands out most in my career is how much monday.com invests in training, coaching and development, which is critical to building successful salespeople, not just in their role, but throughout their career.

It starts on day one. Onboarding is structured around the business, products, customers and what success looks like. In other organizations I’ve worked for, onboarding can feel like a race to get a rep into the field. Here, the emphasis is on long-term success.

That investment continues beyond onboarding with weekly training sessions, plus Agentic Week, a week dedicated to helping employees understand AI, talk about it with customers and use it.

We also rolled out a new career framework, a self-service tool bringing a rep’s development to life. Reps rate themselves across five criteria, at their current level and the level they’re aiming for, so there’s no guesswork about what “next level” means. A self-assessment produces a real plan reps bring into one-on-ones, grounding coaching in specifics, not vague career chats.

I see my role as making these resources actionable through coaching and deal strategy. Development isn’t one-time; it’s an ongoing investment in our people.

 

 

Related ReadingSales Careers on the Rise: Companies Investing in Skill Growth and Mobility

 

360Learning’s AI-driven platform is designed to enable learning and development teams to create content, automate tasks, boost engagement and more. 

 

What’s it like to work on the sales team at 360Learning?

We’re a fully remote BDR org that runs on a business operating model called “Convexity.” Instead of decisions requiring a chain of management approval, we filter our thinking and actions through a shared set of pillars designed to balance autonomy with accountability. Alongside convexity is our employee motto: your life, your way. Reps set their own schedules, take time off whenever they actually need it and work from home or at a reimbursed coworking spot, whatever makes them feel most capable.

 

“Reps set their own schedules, take time off whenever they actually need it and work from home or at a reimbursed coworking spot, whatever makes them feel most capable.”

 

There’s no traditional manager checking anyone’s inbox here. In fact, there’s no “manager” title anywhere in our company. We hire people as decision-makers from day one, so leadership works more like a pit crew than a boss: sharp feedback, clearing blockers, building new campaigns and testing new tools, and fixing whatever’s broken behind the scenes so reps can move fast. That’s a lot of freedom to hand someone early in a sales career, and it takes real accountability to run with it. Most people coming from more traditionally micromanaged roles might take a minute to adjust and really believe it, but once it clicks, it’s hard to imagine working any other way.

 

What does career growth look like for sales employees on your team?

Growth here isn’t gated by tenure. Everyone starts as mid-market BDRs, our highest volume segment, where the sheer number of conversations sharpens a rep’s pitch and their read on buyers. From there, reps earn a move to enterprise: Quotas actually go down, giving them room to work bigger, slower deals and start collaborating directly with account executives and key account managers, giving them exposure and face time with other roles in sales.

That’s also when reps start our Career Readiness Program, a lighter version of the onboarding for whatever’s next, usually account executive, account manager or customer success, providing enough to walk into the interview ready, but not enough to slow them down in their own role. They finish the rest once they land the role.

Most sales orgs make people wait out a year or two before even discussing advancement. We skip that part. The bar is simple: one strong quarter in mid market and they can move up when an opening is available, which is the same for enterprise reps considering whatever’s next. Top performers also earn travel to join the tradeshow team, go to dinners and build real relationships with AEs and leadership.

 

What training, coaching or resources help sales employees succeed and advance?

We ramp people up slowly and keep sharpening them forever. Onboarding runs for three months: two weeks of pure training up front, then blended training and live work for the rest of the first 90 days.

Most places only invest in people when they’re new or underperforming, then leave them alone once they’re doing fine, until they plateau, get bored or start looking elsewhere for growth. We’d rather keep everyone sharp the whole way through. In practice, that means peer role-play, AI-assisted call coaching, team call reviews, live and agency-led training sessions and bite-sized lessons in our app, every quarter. Reps even run their own weekly lunch-and-learns, teaching the skills they’re most excited about so people are learning from others actually doing the job, not just from their coach. And best of all, once a year, the whole sales org flies somewhere warm for a week of team-building and hands-on workshops, with leadership and individual contributors running sessions together.

 

 

Achieve is dedicated to helping consumers build a better financial future for themselves by enabling them to find the right financial solution, such as a personal loan, a home equity loan, debt relief or online resources to help them more effectively control their expenses and save money. 

 

What’s it like to work on the sales team at Achieve?

Working on the sales team at Achieve Lending is fast-paced, challenging and incredibly rewarding. The pace keeps you engaged, and the day goes by quickly because every conversation brings a new opportunity to help someone improve their financial future. Every member’s situation is different, so no two days are ever the same.

Our job isn’t simply to close loans — it’s to understand each person’s goals, educate them on their options and help them make the best financial decision for their future. We take pride in providing a true white-glove experience from the first conversation through funding, making sure every member feels informed, supported and confident throughout the process.

One of the things I value most is how connected our leadership team is to the frontline. We spend time listening to calls, talking with our teams and learning directly from the people who serve our members every day. Their feedback helps us improve because they’re the closest to our members’ needs. That creates a culture where people feel heard, supported and empowered to make a difference.

 

What does career growth look like for sales employees on your team?

Career growth is something we take seriously because we want people to build careers here, not just hold a job. We love promoting from within and take great pride in seeing people grow into leadership and other roles across the company. At the same time, we know great talent and new ideas also come from outside Achieve, and that balance makes us stronger.

We provide leadership development opportunities and encourage employees to learn about different parts of the business. No one is expected to stay in one lane forever. If someone wants to grow, we’ll help them explore where their skills and interests can have the greatest impact — for both their own career and the company. Our goal is to help people find the right fit, not limit what’s possible.

 

“We provide leadership development opportunities and encourage employees to learn about different parts of the business. No one is expected to stay in one lane forever.”

 

What training, coaching or resources help sales employees succeed and advance?

The best training comes from working alongside leaders who genuinely care about your success. Our managers are actively involved in coaching, reviewing calls, celebrating wins and helping team members work through challenges. Coaching isn’t something that happens once a month — it’s part of our daily routine.

Learning also doesn’t stop after onboarding. As the lending market changes, we continue to invest in training, so our teams stay informed and confident in serving our members. We also encourage employees to share ideas and feedback because the people having conversations with members every day often have the best perspective on how we can improve. When people feel supported, challenged and listened to, they become better professionals — and that’s good for our employees, our members and our business.

 

 

Boomi’s platform integrates applications, APIs, data and AI agents to help enterprises achieve agility, efficiency and innovation at scale. 

 

What’s it like to work on the sales team at Boomi?

Challenging in all the right ways! We’ve got an incredible product, an established customer base and a rapid pace of innovation. In order to keep up, sellers need to continuously raise the bar for themselves. Thankfully, you’ll be surrounded by equally brilliant people who will support and drive you to be your best.

 

What does career growth look like for sales employees on your team?

In the sales development function, we are proud to promote about one-third of our reps internally each year. Most commonly, that’s into our account executive and account manager roles, but we’ve also had promotions to other teams, including marketing, customer success and professional services.

 

“In the sales development function, we are proud to promote about one-third of our reps internally each year.”

 

What training, coaching or resources help sales employees succeed and advance?

At Boomi, we’ve been able to consistently progress talent for a few reasons. First, we place a strong emphasis on managers serving as coaches, working alongside SDRs to give real-time feedback and support skill development. Second, we’ve partnered with our enablement team to build an “AE Readiness Program” required for advancement, which focuses on the specific skills SDRs will need to be successful as AEs, which they may not have had the opportunity to develop in their current roles. Lastly, because of our strong track record of internal promotions, we have created a network of SDR alumni eager to support future SDRs in building their careers at Boomi.

 

 

Identity Digital offers the world’s largest domain extension portfolio in an effort to help brands and people regain ownership of their digital identities.

 

What’s it like to work on the sales team at Identity Digital?

It’s busy, dynamic and honestly just a really great puzzle to work on every day. Fast-growing companies like Identity Digital need efficient systems, which is why I enjoy revenue operations, as it lets me solve scaling challenges. 

The team gives you a lot of trust and autonomy to try new workflows and see what works. It’s perfect for anyone who likes playing with data, wants to streamline routine tasks through automated workflows and genuinely enjoys building smoother processes behind the scenes.

 

What does career growth look like for sales employees on your team?

Growth is centered around expanding technical skills through continuous learning and certifications. The process is highly collaborative, with leadership encouraging open dialogue and regular check-ins to map out professional goals. This consistent communication ensures clear alignment on milestone achievements, while the company provides the necessary resources and tool training to facilitate advancement.

 

“The process is highly collaborative, with leadership encouraging open dialogue and regular check-ins to map out professional goals.”

 

What training, coaching or resources help sales employees succeed and advance?

Recently, training to use new AI tools has been instrumental in driving efficiency, both within my own role and supporting the wider revenue team. We prioritize open, transparent communication to ensure that whenever a new workflow is implemented, it is properly integrated and embraced by our account managers. Our leadership heavily values employee feedback, meaning we always have a voice in shaping which resources are provided. To manage this continuous evolution, I am encouraged to block out dedicated time on my calendar for learning. In an environment where AI is advancing daily, maintaining curiosity and an adaptable mindset is key to professional growth and success on the sales team.

 

 

Rundoo’s AI-native point-of-sale system is designed to help independent paint and hardware stores win customers, streamline operations, and grow their businesses. 

 

What’s it like to work on the sales team at Rundoo?

It’s energizing. With the leadership we’ve built, truly nobody will ever ask you to do something they haven’t and won’t still do themselves, myself included. I feel it should be this way in any sales organization. I’ve been a part of many where that’s not the case, both as an SDR and as an AE, and I think it’s important to be leading from the front, regardless of your title, tenure or anything else. It’s rewarding and validating. Being able to be a part of an organization and a team where your work truly matters, and being able to see the downstream effects and the impact of the effort you’ve made is a feeling money can’t buy. We’re able to grow and develop together, learn from other members of our team as well as others, and learn new strategies and approaches in real time without having to worry about micromanagement or someone looking over your shoulder. It’s transparent and aligned. Everyone is in the know at all times, and we’re all aimed toward the same North Star and the same goals for the company. While our individual motivations may differ here and there, we’re all aligned on hitting our goals, and through transparent and honest communication, we all know the role we play.

 

“Everyone is in the know at all times, and we’re all aimed toward the same North Star and the same goals for the company.”

 

What does career growth look like for sales employees on your team?

On my team, career growth is and always will be one of the main motivators, and if it’s not, this may not be the right team. When clear guidelines to growth and trajectory aren’t present, complacency is inevitable, and that’s why our philosophy and plan for internal promotions are very strategically, thoughtfully and transparently laid out. 

My team has had two members make their way to account executives here at Rundoo, and there are a few others who aren’t far behind them. I feel lucky and grateful to be able to play a part in establishing a baseline in how they approach and go about the sales process as SDRs, help them refine themselves in that position, and then train them and help prepare them for the account executive role. It wasn’t too long ago that I was an SDR working hard to get a chance at the account executive role, and once I finally got the chance, I was able to excel quickly, and I love being able to help members of my team take that same jump in their careers and ensure it’s done as thoughtfully and intentionally as possible. I have no doubt the future of the account executive team is currently on my team getting prepared, and I couldn’t be more excited about it.

 

What training, coaching or resources help sales employees succeed and advance?

On my team, I have weekly one-on-one meetings with every member of my team, no exceptions, where I provide coaching and feedback relevant to their tenure, their strengths and weaknesses, and go through specific examples to highlight and positively reinforce good habits and muscle memory. We also have a weekly call coaching meeting, where we listen to some good calls from the team and some that need work, and go around the room and give feedback to one another and share perspectives, as well as a weekly product knowledge session to ensure we’re staying up to date on how our product is improving, and the key reason why we continue to win against our competition. We also do daily call blitzes, where my team pairs up and makes calls out loud with one another to see what other approaches are working and how they can improve or try new things. We also have an incredible tech stack, as well as several vibe-coded domains and tools built by myself and other members of our leadership team to streamline processes and make things as efficient as possible in our day-to-day work. We have an end-of-day sync as well to go around the horn and hear how everyone’s day went and what they’re excited about for tomorrow.