The Evolutionary, Nuanced Nature of Being a Sales Pro in Tech

Like a game of chess, sales is a complex undertaking. Learn how sales pros at three Colorado tech companies navigate the day-to-day highs and lows of their roles while growing in the process.

Written by Olivia McClure
Published on Mar. 28, 2024
The Evolutionary, Nuanced Nature of Being a Sales Pro in Tech
Brand Studio Logo

When Janessa Robbins shows up to work each day, she feels as though she’s heading into a hard-fought, albeit thrilling, game of chess. 

“There’s research, observation, problem-solving and constant learning,” explained the business development representative. 

These characteristics of a typical workday are the reasons why Robbins entered the sales field in the first place. At Peaksware, she gets to accomplish these feats and more while doing what she enjoys the most: supporting others. 

“I’m a social person who loves helping people reach their goals or succeed in their business,” Robbins said. 

But even a job filled with so much passion can be challenging at times. Choozle Account Executive Jamie Cotton knows this well, as he stays busy gauging how to tailor his support to each of the company’s specific customers. 

“There’s no universal solution or one-size-fits-all approach,” he said. 

By understanding customers’ unique needs, Cotton can help them more effectively reach their target audiences. And in turn, he has the chance to strengthen his own skills, supported by both experience and Choozle’s formal professional development opportunities. 

Being a sales professional in tech is a nuanced discipline, marked by the ability to influence others and oneself at the same time. Below, Robbins, Cotton and Freshworks Senior Manager of Revenue Enablement Julie Douglas describe their day-to-day work, the highs and lows of their roles and the opportunities they have to grow at their respective companies. 

 

Julie Douglas
Senior Manager of Revenue Enablement • Freshworks

Freshworks’ software solutions are designed to help businesses easily and quickly support their customers and employees. 

 

What does a typical day look like for you?

I lead revenue enablement for North America, and there’s no such thing as a typical day. My activities and day-to-day work vary significantly depending on the time of year, business priorities and projects we’re focused on. For instance, on a given day, I may be running a prospecting workshop with our business development team, creating content for an upcoming event, meeting with my team to discuss our priorities for the next month or connecting with sales leaders and reps to discuss upcoming enablement and gather feedback on programs and assets.

 

What’s your favorite part of your job, and what do you consider the most challenging aspect?

My favorite part of my job is designing and delivering programs that make an impact on sellers and how we engage with our customers. I’ve spent most of my career in tech sales, and with the rapid pace of change, programs that drive continuous learning and readiness are critical. It also helps that I work alongside passionate, intelligent and hardworking people whom I enjoy interacting with every day. 

I’ve spent most of my career in tech sales, and with the rapid pace of change, programs that drive continuous learning and readiness are critical.”

 

There’s a lot of exciting work to do at Freshworks, which leads me to the most challenging aspect of my role: prioritization and determining where to focus in order to make the biggest impact. While this is always a challenge in an enablement role, I start with our overall goals in North America and work backward from there, analyzing where the biggest opportunities are and incorporating feedback from leadership and cross-functional teams.

 

What opportunities for advancement are there in your position at Freshworks? 

At Freshworks, we’re encouraged to take charge of our own career development or, to quote our chief people officer, “Be the conductor of our own orchestra.” The company provides numerous resources and opportunities for employees to grow in their careers. A large part of my role and focus is developing our sales talent to not only help them reach their objectives, but equip them with the skills they need to advance in their careers, whether their goal is to become a manager, move upmarket or shift into a different type of selling role. One opportunity that I take advantage of is membership in our Women 360 employee resource group, which offers career development events and mentorship programs. 

 

 

 

Janessa Robbins
Business Development Representative • Peaksware

Peaksware develops software solutions that help athletes and musicians track individual progress and measure performance. 

 

What does a typical day look like for you?

My role is to find prospective customers who can potentially achieve success by using our products. We’ve been doing this long enough to understand what defines an “ideal customer.” Based on that criteria, my day-to-day work consists of me using social media and email to find prospects. 

Once I find the right prospect, there’s a fair amount of research that goes into confirming that we’re a fit, and most importantly, I make sure that I understand exactly how we can help them before I reach out to them. A certain percentage of the prospects I reach out to are interested in learning more, and when that happens, my job is done — well, mostly. I set up a meeting between that prospect and our account executive team so they can chat with the prospect, learn more, confirm they’re a fit and put a plan together to move forward. 
 

What’s your favorite part of your job, and what do you consider the most challenging aspect? 

I started in sales because I enjoy building lasting relationships, and I thrive in a fast-paced environment where each day presents a unique set of challenges and opportunities. As I’ve grown in my role, I’ve learned more about the nuances of why I enjoy the day-to-day life of working on Peaksware’s sales team. I find joy in identifying the right prospects, understanding their needs and creating effective communication strategies that resonate with them. It’s great to see my hard work pay off in objective terms by meeting and exceeding quotas and seeing our coaches onboard and succeed. 

The most challenging aspect of my job is getting people to respond to outbound sales messages. It’s tough to craft a message that will resonate with someone so deeply that they respond. I’m a competitive person who loves to research and understand people’s needs and how I can best meet them. When I run into challenges, I ask myself, “How can I better articulate what we have to offer them?”

I find joy in identifying the right prospects, understanding their needs and creating effective communication strategies that resonate with them.” 
 

What opportunities for advancement are there in your position at Peaksware?

There are quite a few different paths to take in my career at Peaksware. Mastering sales requires the development of both soft and hard skills that can transfer to different roles or career paths. The company helps me focus on my professional goals and aspirations and works toward generating a plan to ensure that I have the opportunity to make progress in my career. That’s just one reason, albeit a big one, that got me excited about joining Peaksware. 

I’ve only been here for six months, yet I’ve already had numerous conversations about my career development. At the same time, the team consistently makes time to work with me, coach me and help me refine my skills as I grow in the role. I’m excited about my future at Peaksware and the salesperson I’m becoming in the process.

 

 

 

Jamie Cotton
Account Executive • Choozle

Choozle’s digital advertising platform enables businesses to create programmatic advertising campaigns across video, mobile and other mediums. 

 

What does a typical day look like for you?

As an account executive at Choozle, my schedule is packed with exciting opportunities to maximize digital advertising impact for premier agencies and leading brands. My primary responsibility involves establishing new partnerships, which requires a careful balance between prospecting new business, providing education and strategizing with our clients on upcoming campaigns. 

Internally, I collaborate with Choozle’s team of media experts to develop and refine digital campaigns. I feel privileged to spend my days engaging with brilliant minds, solving complex marketing challenges and achieving tangible outcomes.

 

What’s your favorite part of your job, and what do you consider the most challenging aspect?

The most rewarding aspect of my job is guiding our clients through the dynamic landscape of adtech. Given the constant evolution of digital advertising, strategies that proved effective yesterday may no longer work tomorrow. Consequently, we’re constantly exploring innovative ways for brands and agencies to connect with their target audiences. 

Simultaneously, this proves to be the most challenging aspect of the job. Each business is unique, requiring a tailored approach for every campaign to achieve the desired outcomes. There’s no universal solution or one-size-fits-all approach. Therefore, we engage in thorough testing and iteration and rely on comprehensive data provided by Choozle’s reporting to identify areas where we can optimize our impact.

The most rewarding aspect of my job is guiding our clients through the dynamic landscape of adtech.”

 

What opportunities for advancement are there in your position at Choozle? 

At Choozle, account executives are offered a variety of career development perks and opportunities. There’s a fully scoped career track, which is broken out by positions and responsibilities. It’s a great way for me to keep track of my development within a formal framework. Furthermore, Choozle also offers training with top technologists in the industry and full access to LinkedIn Learning courses, which allow team members to develop skills both within and outside of sales. We pride ourselves on being at the forefront of the adtech space, so staying sharp allows us to anticipate potential threats and strategize around them.
 

 

Responses have been edited for length and clarity. Images provided by Shutterstock and listed companies.

Hiring Now
Skillsoft
Edtech • HR Tech • Information Technology • Software • Consulting