Landing a job in tech sales is like discovering the “power couple” of careers.
According to Built In, the average annual base salary of an account executive in the United States is $99,009. Add that to the fact that 62 percent of executives who participated in a 2024 Deloitte survey feel so confident about the upcoming growth of the tech industry that their businesses are willing to take greater risks, and you’ve got a career match made in heaven.
With these statistics in mind, it’s easy to see why many professionals have found themselves working in tech sales. But the question remains: What does it take to get there?
In truth, the academic and professional journeys people take before winding up in this field are inconsequential; it’s the skills they build during those journeys that help them succeed. For Riskified Business Development Representative Audrey Cavanah, having a desire to learn is key to thriving in tech sales, while Gynger Account Executive Ben Kaplan believes creativity is essential for standing out.
But ultimately, a company’s sales culture plays a large role in a tech sales professional’s ability to continuously evolve. Comcast Advertising takes growth seriously in its sales culture, which is why East Coast Sales Lead Taylor Chamberlain has been able to hold a variety of roles since joining the company.
These three tech sales professionals prove that, with the right skills and culture, anyone can break into tech sales — and thrive. Read on to see what Cavanah, Kaplan and Chamberlain had to say about how they broke into tech sales, the best skills and knowledge to have and how their companies’ sales cultures make it easy to grow.
Comcast Advertising’s three brands — Effectv, FreeWheel and AudienceXpress — are dedicated to helping other brands connect with audiences through TV advertising.
Give us a snapshot of your career so far. What has been your path to tech sales?
I started my sales career on the linear side at a network and took a promotion to a newly forming advanced TV team. Though it was a risk, it became a driving force in my career. Transitioning from linear sales associate to a planner in programmatic adtech allowed me to build my skills in selling, deal creation and optimization. After about three years in the advertising industry, I joined FreeWheel, the advertising management arm of Comcast Advertising, as an account manager, where my programmatic knowledge made the transition seamless.
A year into my time at FreeWheel, we built an independent demand team, allowing me to leverage my programmatic and account management experience while challenging my sales skills by working with new independent agencies. After a year and a half of strong results and contributing to the independent agency team’s growth, I stepped into an East Coast sales lead position.
What advice would you give someone looking to break into tech sales? Are there any must-have skills or knowledge that helped you get the job?
The media and advertising industry and FreeWheel are constantly evolving, which is due in large part to the innovation and drive of our teams, so there’s always something new to learn and stay ahead of the curve. Do your research, show your eagerness, be “coachable” and enjoyable to work with, ask questions and don’t be afraid to give your input.
“Do your research, show your eagerness, be ‘coachable’ and enjoyable to work with, ask questions and don’t be afraid to give your input.”
How would you describe the sales culture at Comcast Advertising? How have you grown professionally as you’ve worked in tech?
There’s a lot of noise in programmatic advertising right now, and it can be confusing. At FreeWheel, we view our sales team members more like consultants than salespeople, fostering a collaborative team environment where everyone is eager to work together to support our clients and the industry. As the leading ad server for streaming TV, it’s our responsibility to educate, upsell, manage deals and inform clients about new capabilities. Adopting a sales approach focused on the question, “You’re already partnering with us; how can we further enhance your experience?” has proven to be successful and strengthens FreeWheel’s credibility in the marketplace.
Throughout my career, I’ve had the opportunity to take on a variety of roles that have expanded my expertise and leadership abilities. Starting as a linear account manager, I built a strong foundation in media sales before transitioning into more complex positions like advanced TV sales planner and an account manager at FreeWheel. As an independent account executive at FreeWheel, I honed my client management skills and business development acumen. Now, as the FreeWheel East Coast sales lead, I oversee a team of five.
Riskified’s AI-powered platform helps e-commerce businesses mitigate fraud and policy abuse and improve customer retention.
Give us a snapshot of your career so far. What has been your path to tech sales?
When I graduated from college, I joined a business management firm that handled both business and personal affairs for high-net-worth clients. I was an account manager and was responsible for clients’ bookkeeping, vendor management and real estate portfolio needs. Shortly after that, I moved to NYC, where I began working for a recruiting firm, hiring VP and C-suite sales executives within the fintech industry. This was a 360 recruitment role, which involved identifying open positions and matching suitable candidates until the job was successfully filled. In a sense, it was a sales job, but not your traditional sales role.
I became familiar with Riskified because it’s well known in the industry, and I consistently heard positive feedback about the company. When I decided to pursue a business development role and saw there was an opportunity open at Riskified, I knew it would be an excellent fit for my career aspirations.
What advice would you give someone looking to break into tech sales? Are there any must-have skills or knowledge that helped you get the job?
The most valuable piece of advice I can offer is to cultivate a strong desire to learn while maintaining resilience. Navigating certain technologies can be quite challenging, especially when these technologies aren’t topics of daily conversation with friends or family. Therefore, it’s crucial to ask questions and recognize that it’s perfectly fine to not have all the answers. In sales, facing rejection from prospects is a common occurrence, which makes it essential to stay resilient and continue honing your skills.
“It’s crucial to ask questions and recognize that it’s perfectly fine to not have all the answers.”
How would you describe the sales culture at Riskified? How have you grown professionally as you’ve worked in tech?
My experience at Riskified has been extremely positive. My managers and teammates are incredibly supportive and helpful; everyone is always willing to offer advice or collaborate on various projects. While salespeople are often seen as persistent, we take a highly strategic approach at Riskified, focusing on establishing strong relationships with prospects from the very beginning.
This has led to significant professional growth for me, largely due to the consultative approach we adopt with both customers and prospects. By actively listening and engaging with clients, I’ve come to understand their unique needs and objectives more deeply. This experience has taught me the importance of thinking creatively and strategically to address the specific challenges of each account I work on. I’ve realized that tailoring our strategies to fit individual circumstances is key to fostering lasting relationships and driving success.
Gynger’s platform helps businesses manage technology expenses while improving cash flow.
Give us a snapshot of your career so far. What has been your path to tech sales?
During college at University of California, Santa Barbara, I studied anthropology and earned my degree. I stumbled into tech sales by chance after experimenting with a few business ventures while still in school.
After graduation, I moved to Dallas to help a family friend by building out their sales team. However, being inexperienced and effectively managing myself didn’t give me the growth I needed, so I decided to seek guidance from industry professionals. This led to a role as a channel account executive at Brex, where I honed my sales skills and gained valuable insight into the business needs of chief financial officers and CEOs as well as the dynamics of the VC and startup ecosystem.
After two years at Brex, I realized I wanted to make a bigger impact and contribute to building something new, which brought me to Gynger as one of the earliest employees.
What advice would you give someone looking to break into tech sales? Are there any must-have skills or knowledge that helped you get the job?
For anyone looking to break into tech sales, my advice would be to focus on developing strong communication skills and the ability to understand customer pain points. You don’t need to be a technical expert, but you do need to understand the product you’re selling and how it solves specific problems for your customers. In my case, having a good grasp of financial solutions and how businesses manage cash flow has been key.
Whenever you’re looking for a new tech role, treat it like the hiring manager is a customer and you’re trying to close a deal. I stood out among the other candidates at Gynger because I studied the industry, had a pitch nailed down and sent champagne to the company’s office. Be creative; you’ll stand out, and it makes looking for a new job much more enjoyable.
“Be creative; you’ll stand out, and it makes looking for a new job much more enjoyable.”
How would you describe the sales culture at Gynger? How have you grown professionally as you’ve worked in tech?
At Gynger, we operate in a startup environment where everyone is expected to take full ownership of their deals, but there’s also a strong sense of collaboration. Even though you manage your own pipeline, the team works closely together to ensure we’re all successful, whether that means troubleshooting a client’s issue or strategizing on a large deal. It’s a hands-on, all-hands-on-deck culture where you learn to be resourceful and proactive.
I’ve grown by becoming comfortable speaking with businesses of any size. My previous experience was focused on startups, but at Gynger, I had to adapt quickly as larger clients came into the mix. This required me to develop a different approach, learning how to handle more complex deals and long-term customer relationships. The key is to build genuine relationships where you’re seen as a partner helping their business grow rather than just someone trying to hit a quota. It’s about offering solutions that improve their operations, not just making a sale.
