Building a Diverse Team and Culture

Jun 04, 2023
Building a Diverse Sales Team and Culture

As a white male who joined an industry dominated by other white males but comes from a household of dominant women, I wondered in my early years why there weren't more women in sales. This became a focus for me as I began working in leadership roles and leading the recruitment strategy and process.

One thing I knew for sure was that we were never going to focus on hiring quotas or anything that would interfere with hiring the people we believed to have the highest probability of success in the role. We structured our process in such a way that each person involved in the decision was focused on answering one question; why can't this person be a great salesperson?

By changing our mindset away from looking for people we thought could be great at sales, I insisted that we begin thinking about reasons a candidate can't be great at the job. By doing this it allowed us to focus on reality rather than fantasy. We can easily use our imaginations to create an illusion that a person will be great at sales, but often we have no foundation for believing this other than we actually like the person and want it to be true.

When we shift our mindset in the opposite direction I believe we obtain better and more accurate results because we force ourselves to have the conversations that matter most with our hiring teams, which are the reasons a candidate potentially cannot be great at the job. This saves time, skips straight to the points that matter, and forces your hiring team to avoid bias. It also forces them to bring their biases to their internal surface since they have to explain verbally why this candidate cannot do the job, which becomes difficult to do if your reasoning is more of a bias than a reality.

I implemented this strategy at SinglePlatform and evolved it even further at Doctor.com and Aircall. While I'm tremendously proud of the diversity and cultures we built at these companies and the results are far improved from prior industry norms, there's certainly more improvement to be made, but the trends are optimistic.

SinglePlatform 2013 - New York, NY

At SinglePlatform when I was promoted to Head of Sales Training my objective was to hire, onboard, and train 10-20 new salespeople each month. We were going through a massive growth phase after being acquired for $100M by Constant Contact. Because of this I was promoted from top salesperson to take the lead on hiring and on-boarding these new classes of salespeople. The economy was on the up-rise and we had no shortage of candidates but we had plenty of issues to navigate internally to steer the ship in the direction of diversity.

We achieved a lot of success by hiring a lot of people who were all very similar, but as we started experimenting with hiring folks outside of that normal box we began seeing even more success. So I decided to double down on the effort and that's when I first introduced the concept of "tell me why they can't do the job" which was a shift from our normal approach of discussing reasons people could potentially be good at the job, and leaving the reasons they can't as secondary.

The result was a significant increase in female hires in comparison to prior months as well as candidates from other employment and ethnic backgrounds.

Doctor.com 2017 - New York, NY

A few years later, as VP of Sales at Doctor.com, after bootstrapping our way through the seed stage we eventually raised a Series A round of funding and began a hiring protocol to grow the sales team. I once again introduced my hiring team to my approach and we continued to see the same success as we saw at SinglePlatform.

Toward the end of my hiring streak at Doctor.com I began to formulate a new theory that we needed to begin focusing more on our recruitment strategies if we wanted to achieve an even more diverse team and culture. This meant avoiding hiring quotas and aiming for hiring people from specific backgrounds, but instead deploying recruitment strategies that would result in a diverse candidate pool, which should then result in a diverse team and culture without the risk of hiring someone for the wrong reason (which sets both parties up for failure).

This was the additional tactic I brought into Aircall which I believe to be the most effective path toward building a diverse team and culture.

Aircall 2019 - New York, NY 

At Aircall we were hiring more aggressively but the employment market was also getting significantly more competitive in NYC. Attracting top talent was becoming more difficult because there were a lot more venture-backed startups competing for the best hires. Because of this I knew we needed to focus on a the practices I outlined above but we needed to turn it into a flywheel model where our top people were attracting more top people.

Unfortunately this isn't as easy as asking people to refer their friends. This works sometimes but usually the notion that "great people know more great people" isn't actually an effective recruitment strategy in a competitive market because great people also already have great jobs.

So I knew we had to think bolder and that's when I decided we needed to utilize our great people in the interview and recruitment process by matching like-minded personalities and embracing the concept of "great people know great people" but using it more in the direction of "great people want to work with great people".

So for example, we would focus our recruitment efforts in a diverse set of areas, with campaigns focusing on certain genders, demographics, work history, personality traits, experience level, etc. but then when the candidates were scheduling interviews we would pair them with existing team-members who we believed would have commonalities and reasons to "get along" or relate to one-another.

This allowed for our candidates to feel like they were entering an environment that was inclusive of people who had things in common to them and allowed them to envision their future life as a part of the team in a positive light.

While building and recruiting teams of diverse backgrounds and cultures is a challenge worth focusing significant effort, it's important never to let it become the core focus of hiring and building a great team. That is why I've always chosen to direct my efforts towards these 3 things, which help to avoid hiring people for the wrong reasons:

  1. Focus recruitment on generating a diverse pool of applicants and candidates  top of funnel
  2. Focus interviews on identifying reasons candidates can't be great at the job → mid-funnel
  3. Utilize existing team-members to create an inclusive candidate experience → bottom funnel

By focusing our efforts and strategic decisions on these 3 objectives I believe we were able to significantly reduce our unconscious bias, attract a more diverse applicant base than our local competitors, and achieve a more inclusive hiring process and team culture.

This is a journey that has made much progress throughout the B2B SaaS industry over the last 10 years but there is plenty more progress to be made. I believe that by deploying these 3 practices the industry will continue to move in a direction of expanded diversity across all realms of consideration and this will continue to have a positive impact on the industry, it's employees, it's customers, and the world.

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Happy Selling,

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