How to Build a World-Class Sales Team

Rally Ventures
4 min readNov 8, 2023

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In a recent masterclass for the Rally portfolio, a panel of Rally Tech Partner sales experts talked about sales organization design, comp strategy, how to build early sales and marketing and how to foster a great sales culture at your company.

Nailing your go-to-market (GTM) strategy is critical, especially in our current macro economic environment. What we’ve seen across the Rally portfolio is that software sales cycles have elongated and there is a renewed focus on how to efficiently and successfully scale your GTM team. One important topic we talked about is what to look for when making early-stage hires.

Jeanne DeWitt Grosser is the Global Head of Partnerships at Stripe and a Rally Technology Partner. She built much of Stripe’s original sales engine, is a former startup CRO and a SaaS+ expert with 15+ years experience in SMB and large enterprise sales.

Jeanne talked about how she often sees founders hiring account executives who are an intellectual general athlete. These types of AEs tend to have more of a business operations background, but not necessarily a lot of direct sales experience. They tend to work well because in the early stages of building a company you’re trying to figure out product market fit and where to scale. Having someone who is analytical with great pattern recognition is helpful.

The common error here is companies will over index on that type of hire. What you want to do is pair that person with someone who has legitimate sales experience. Sales knowledge is a skill you acquire, just like coding is a skill you acquire. It’s not something that can be learned overnight, and you need someone in this role with a proven track record who can generate revenue.

On the sales leadership side, the mistake she generally sees folks make is hiring a person too junior or too senior. Her advice is to find someone whose current job is where you’ll need to be in two years. If two years from now, you think you’ll have a 30 person sales organization, find the person who is currently managing a 30 person org. If you hire too junior, you’ll outgrow them quickly. If you hire too senior, they’ll likely bring large enterprise sales strategies that won’t work well at an earlier stage company.

Elizabeth Benz is the Chief Sales Officer at Jamf and a Rally Technology Partner. She has an extensive background in business development, sales operations and delivering exceptional sales and margin growth.

Liz talked about how one of the tactics that has worked well for her in hiring is thinking about people’s motivations. You can hire someone early in their career if they’re highly motivated, goal oriented and strong willed. But you also need someone on your team with the ability to develop them into a good seller. Liz typically hires on potential vs what they’ve already accomplished and it’s worked out tremendously well in her career.

For the sales rep position, she likes someone who is either a subject matter expert or has experience talking to the buyer persona. For example, if they’re selling to CFOs, she loves hiring people from KPMG or E&Y. People can be developed into great sales reps if they have that sales DNA potential, business acumen and a great leader to guide their development.

In terms of leadership development, Liz is a big believer in career pathing. People have to see a path and a future at your organization, especially during economic times like this when things are harder. She doesn’t look for the best seller to lead the sales organization, but someone who has empathy and can keep people engaged. They have to know how to put together and motivate a team.

Justin Kaufenberg is a Managing Director at Rally Ventures. He is also the co-founder and former CEO of SportsEngine, an ultra high volume inside sales organization that landed 25,000 unique customers during his tenure.

Justin expanded on the importance of making the right early-stage sales hires and some real-world examples of building a strong sales organization. He agreed with Liz and Jeanne that a person with the right experience and attitude is more valuable than someone with big name logos on their resume. He’s been guilty of both hiring someone who came from a large incumbent leader in the space who wasn’t able to scale down and hiring someone who had an iron stomach for startups but didn’t yet have the experience to scale up the GTM team. The sales leader position really is a goldilocks position for the stage you’re at. It’s not easy to find.

His advice is to spend time on reference checks before you make the hire. It’s the best way to get to the truth of whether someone will be a good cultural leader and fit for your organization. During the interview, it’s hard to parse through people who can look similar on their resumes, but are very different below the surface. Instead of trying to figure it all out during the interview process, over index on the reference checks. Spend time with the people who’ve previously worked with and for them. It could take up to 5 or 6 reference checks to determine if they’re the right fit for your team and culture, but it’s worth the upfront effort.

The content for this article was created from a recent masterclass on sales. Rally Ventures occasionally hosts masterclasses for our portfolio companies, led by experts and industry veterans.

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