4 Local Leaders on How to Build – and Scale – Successful Sales Teams

Leaders at Mendix, BitSight Technologies, ProfitWell and Akeneo discuss how to manage growth while cultivating a strong team culture and the importance of inquisitiveness in sales.

Written by Olivia McClure
Published on Jan. 13, 2022
4 Local Leaders on How to Build – and Scale – Successful Sales Teams
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As senior vice president of sales for the Americas at Mendix, Tim Brown knows what it takes to build out and scale a sales team. For him, creating a winning organization doesn’t begin and end with recruitment, although that is part of the process he employs at the low-code app development platform. 

“To ensure we identify, attract and retain talent, it’s paramount to have solid leadership in place,” Brown said. 

According to Brown, a successful sales team also comes down to identifying the qualities that define strong salespeople. The ideal salesperson should embody a sense of purposeful inquisitiveness, which feeds the potential for future growth and innovation. 

“This should be a shared trait across the business in order to achieve full organizational value and foster a culture where talented people wish to stay and grow,” Brown said. 

Yet simply seeking out the right talent isn’t the only way to cultivate a strong sales team. Jim McInerny, vice president of sales at information security risk management company BitSight Technologies, said it’s equally crucial to offer team members ample opportunities for growth. That’s why his team invests heavily in each new class of sales development representatives, giving them space to develop their careers. 

When it comes to maintaining steady team growth, leaders must do more than simply empower their teammates. According to Michael Bender, vice president of sales for the Americas at product experience management company Akeneo, it’s essential for sales teams to embrace change in order to scale successfully. 

For each of these leaders, creating and managing successful sales teams requires equal amounts of strategy, determination and intention. Built In Boston caught up with Brown, McInerny, Bender and ProfitWell Chief Revenue Officer Peter Zotto to learn how they build successful teams, what they look for in strong salespeople and how they foster a positive culture.

 

Mendix team photo
Mendix
Tim Brown
Senior Vice President of Sales, Americas • Mendix

 

What’s your blueprint for building a successful sales team, and how have you put that blueprint to work in your current role?

Any blueprint begins with knowing what you’re looking for during the hiring process. Communicating a clear profile to both your talent acquisition team and candidates is crucial for success. In our current market, true talent is at a premium. The balance of power has shifted and no longer sits with the employer. Our managers act as strong coaches, advocates and confidantes to their teams and candidates. 

Steve Jobs once said, “It doesn't make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do.” I believe this is the methodology we seek to accomplish at Mendix. Inspiring and empowering talent is key to building a high-performing sales organization. Sales organizations often onboard employees with a front-loaded view of enablement. While there is value in learning through doing, we have seen a greater need for ongoing informal and formal training throughout an employee’s tenure. Overall, it’s crucial to create a strong candidate profile, empower your talent acquisition team, and nurture talent. 

 

What's the most important characteristic you look for in a salesperson, and why? 

Purposeful inquisitiveness. Inquisitive people tend to be intellectually adventurous, creative and ambitious. Regardless of the product, customers appreciate sellers who holistically understand their business, which is best gained through a consultative process driven by inquisition. At Mendix, we seek to engage the customer in discussions that are strategic, transformational and revolve around an element of change management. To successfully navigate our complex landscape and assist our customers, we need those who are purposefully inquisitive enough to piece together puzzles in a demonstrable manner. 

Our salespeople must also have similar traits to our leaders. You can’t hire purposefully inquisitive people at an organization that doesn’t reflect their values at its core. It’s imperative to foster inquisitive behavior by finding time to engage in discussions that often have questions without empirical answers. 

Overall, it’s crucial to create a strong candidate profile, empower your talent acquisition team, and nurture talent.” 

 

While scaling, how do you ensure your team retains the elements that made it successful in the first place?

Maintaining momentum while scaling requires a focus on three categories. First, it’s key to stay true to your profile. Once you define what makes a great hire, it’s imperative that you honor it. Do not settle to fill a team due to pressure from higher-level management. The right people are out there and you need to remain vigilant in finding them and consider all avenues for recruitment beyond traditional ones.

Secondly, put people in a position to succeed. Scaling sales organizations often struggle due to headcount growth fueled by simplified assumptions that more sellers equates to more revenue. This is true to an extent. Yet in order to maintain pre-scale momentum, teams must ensure that all additional heads are put in a position to succeed.

Lastly, invest in people and build and promote your own talent. While scaling, we encourage team members to identify areas of expertise where they can grow as thought leaders. In order to make this happen, our managers must be willing to invest in our people. Part of this investment lies in career growth. Yet understanding individuals’ goals, whether they be financial, professional or personal, is critical for fostering both development and a desire to stay at the company.

 

 

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Jim McInerny
Vice President of Sales • BitSight Technologies

 

What’s your blueprint for building a successful sales team, and how have you put that blueprint to work in your current role?

Building a successful sales team starts with hiring the right people. In today's competitive business climate, it’s critical for sales leaders to constantly recruit, interview and keep a pulse on talent. Recruiting top talent is a process, not an event, which is why the best time to try and find the best talent is when you don't need to. Building dialogue, establishing trust and winning people over takes time, much like running a sales campaign. Part of our blueprint is to continually interview candidates, so that when the need arises, we know who is out there and what their situation might be.

It’s also key to establish and foster a strong sales development program in order to build a successful sales culture. We invest ample time and effort into the SDRs we hire each year because finding those with purpose and confidence helps us accelerate learning and results through a defined career path. We want to hire the best young talent we can find, because over time, that becomes our bench for scaling and backfilling. 

 

What's the most important characteristic you look for in a salesperson, and why? 

Inquisitiveness is the most important characteristic that I look for in a salesperson. Sales is a vocation that requires listening and learning while understanding why something matters. In order to truly dig into a business problem and offer a solution, one must have the conversational finesse to expose underlying pain points and their impact on both the business and stakeholders. As a way to build trust and establish credibility, a strong salesperson needs to be empathetic, genuine and inquisitive in order to understand the true importance of a problem. Salespeople often stay on the surface and miss the opportunity to dig deep to gauge what the consequences are and why they matter. 

Knowing what questions to ask and when to ask them is an important skill. Maintaining an inquisitive nature is critical to building credibility and being recognized as someone who is consultative and thoughtful in their approach. The very best salespeople in the world pride themselves on asking meaningful questions. Questions lead to answers and answers lead to whether an opportunity is qualified or not. 

Building a successful sales team starts with hiring the right people.”

 

While scaling, how do you ensure both your team and the company as a whole retain the elements that made them successful in the first place?

Scale should never be an accelerated proposition, which can have disastrous consequences. Growth should be done in moderation. The expected outcomes and milestones should be gradually and directionally correct yet not risky enough so that the model is doomed if expectations are off. In order for sales to scale, the supporting entourage and infrastructure, such as operational support, clear analytics, marketing and enablement and onboarding, should already show signs of progress and systematic leverage.

The most important aspect of successfully scaling a business is knowing when to grow. In the world of venture-backed technology companies, the pressure to succeed occasionally forces a company to over-invest when the organization has yet to recognize whether they are ready to do so. Some companies string together a few good quarters then decide it's time to scale without knowing why those few quarters were successful. It makes people question whether the company is really onto something or if the market is simply frothy. Therefore, signals can be misleading and the scale, which is typically an over-investment in capacity or headcount, dilutes reality and causes chaos.

 

 

coworkers thinking about an issue
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Peter Zotto
Chief Revenue Officer • Paddle

What’s your blueprint for building a successful sales team, and how have you put that blueprint to work in your current role?

It starts with having the right people. Regardless of the type of blueprint we put in place to execute our sales motion, without the right team to execute it, that blueprint won't work. That’s why I focus on hiring the right people and identify the traits that define successful salespeople. With the proper hiring and onboarding process in place, you can begin to carry out the sales motion.

We operate across three unique teams as part of our larger revenue org. We define them as “zero to lead,” “lead to demo” and “demo to close.” Each of these teams has daily, weekly and monthly goals, from subscribers and engagement to calls booked and trials converted. Yet they are all focused on one specific metric: revenue. Each week, the larger team comes together and discusses what we did last week and what we're currently doing to influence that revenue metric. It holds us accountable as both individuals and teams. ProfitWell is a bootstrapped business without any outside funding, so for us, being smart about each decision mentioned above is what allowed us to build out a successful sales team. 

 

What's the most important characteristic you look for in a salesperson, and why? 

I consider intellectual curiosity the most important characteristic, followed by coachability. Having led sales teams for about 15 years, I have found that the most successful people are those who are genuinely interested in understanding the market, potential customers and those customers’ problems. If someone has that skill as well as the ability to handle constructive criticism, they'll be unstoppable. Executive presence, intelligence and prior success are also great characteristics, yet curiosity and coachability are the most essential qualities. 

It's worth noting that early-stage companies will want to hire salespeople who are more generalists than specialists and have the tenacity to execute a sales motion. More-established businesses can afford to hire specialists, or people with the right experience to execute on the playbook a sales leader has built based on learnings from the last several quarters and years.

Being a leader on a scaling team requires ensuring your teammates are galvanized around a central mission.”

 

While scaling, how do you ensure your team retains the elements that made it successful in the first place?

A leader's skills will be truly tested when a team is scaling. Salespeople will get bored executing the same process every day for an infinite amount of time. It's critical to offer regular opportunities for training and internal promotion. Being a leader on a scaling team requires ensuring your teammates are galvanized around a central mission. Delegating essential parts of the job to individual salespeople, running meetings and training sessions and managing new hire onboarding allows them to learn, fail with a safety net, and experience leadership to determine if they want to move into a management role in the future.

On a practical level, each sales meeting must have accountability. Each representative has to define what they'll accomplish that week and how. The subsequent week includes speaking directly to that accomplishment or lack thereof. This model gives us a default post-mortem of what is working and what isn't and gives everyone a voice at the table.

 

 

Akeneo office space
Akeneo
Michael Bender
Vice President of Sales, Americas • Akeneo

 

What’s your blueprint for building a successful sales team, and how have you put that blueprint to work in your current role?

I've seen success in creating a sales organization that is driven by both individual and team-wide goals. A focus on teamwork encourages people to support, teach and challenge each other. I currently have senior sellers on a team with more junior sellers and business development representatives. They are all connected to each other. It's great to see a seller push their teammate to achieve success. 

I also love what this model does for career paths. BDRs learn directly from junior sellers and are set up for success when a role opens up. Junior sellers learn from senior sellers while senior sellers take on management responsibilities for the team. Everyone gains skills they can take with them into their next role.

What's the most important characteristic you look for in a salesperson, and why? 

The ability to hustle. A great salesperson needs to show scrappiness in every element of the job. They have to drive urgency through every step of the sales process. They must pick up the phone themselves, create their own opportunities, and push their way through every thread of prospects' organizations. They should never be content with their skill set and must continually improve. It's easy to sit back, deal with your leads, hit 80 percent of your goals, and be a B-level player. Real sales success requires hustle.

A great salesperson needs to show scrappiness in every element of the job.”

 

How do you maintain a strong team culture while scaling? 

There are certain things we do to cultivate our culture. We are front and center about our core values: humility, innovation, benevolence, openness and beer. Yes, I meant to say beer. We look for these traits during the hiring process and make sure they are followed from the top down. It’s important for our CEO to ensure that the entire company comes together for a week of fun team-building activities and collaboration. For instance, despite the pandemic, we safely got together in Barcelona last year. By taking part in these types of events, new hires have the chance to truly experience the culture of Akeneo.

 

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

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