GTM Chalk Talk with JV: Scaling and Retaining a Salesforce – Building the Employee Virtuous Cycle

Strategy, analytics, tactics, and all things sales with Jonathan Vassil, Chief Revenue Officer at Toast.

Jonathan Vassil, Tidemark Fellow and Chief Revenue Officer at Toast, is one of the most data-driven, fast-learning sales leaders we know. At Toast, he is rapidly scaling a direct salesforce that has generated over $500m in ARR last year.? In a recent GTM Chalk Talk session, JV shared his experience scaling and retaining a powerful sales team.? If you haven't read our last summary on JV’s insights around building a local GTM team, check it out here. Otherwise, read on for his thoughts on effectively building (and retaining) a high-performing sales team.?

If you would like to sign up to be considered for participation in a future live session, please email us at [email protected].

Key Takeaways:?

The two fundamental sales truths JV lives by:?

1. The margin between great and good is big, and great and poor is huge. As you look for the right sales staff to add, keeping the talent levels high is both more important, and more challenging, than you would think.?
2. The inputs are more important than outputs. Measure and encourage the inputs correctly, and the outputs will follow.

With these truths in mind, for high-growth SMB vertical SaaS vendors, executives should focus on hiring more junior staff who are hungry for opportunity. We hinted at this during our last recap, so without further ado, here are a few of JV’s hiring tips:?

1. You should very rarely poach AEs (account executives) from competitors, instead hire for specific personal attributes.
2. Hiring all sales reps at one level can extend tenure and lower attrition rates.?
3. Don’t fall into the trap of hiring expensive, flashy talent. You want someone who is hungry.
4. “Gritty” characteristics can be measured in a variety of ways during the interview process: The highest correlated factor to success is work ethic. Next is coachability.?One of the best ways to test for work ethic is to utilize a project-based hiring process. The important thing isn’t necessarily the candidate's articulation during the call, but instead measuring how much prep work they did. For example, Toast tells managers there should be a certain number of features mentioned in the first interview, and another number in the second interview. The second interview brings up an important question: did they improve in the second round? This helps measure their coachability.

Once you have made the choice to hire someone, it is equally important to deliver on the promise of opportunity you sold them on. Just as you are selling a value proposition to customers, you want to be selling a value proposition to employees, too. Ultimately, you are selling opportunity, not OTE (on-target earnings). It is critical to make sure there are clear, objective paths to career advancement for your sales team, and you should publicly celebrate team members as they advance through your ranks.?

Finally, you have to be concerned with the performance framework. The tricky part for companies hitting hyperscale is that you can have an AE performing well while not necessarily being a good salesperson if the product is great. Sales leaders need to measure empirically and filter through the noise to keep the right team in place.?

Share your thoughts

We hope you enjoyed this brief recap of another one of JV’s great sessions. If you would like to sign up to be considered for participation in a future live discussion, please email us at [email protected].

The information presented in this post is for illustrative purposes only and is not an offer to sell or the solicitation of an offer to purchase an interest in any private fund managed or sponsored by Tidemark or any of the securities of any company discussed. Companies discussed in these posts may include current Tidemark portfolio companies and/or prior investments made by Tidemark employees while at other investment firms. These companies identified above are not necessarily representative of all Tidemark investments, and no assumption should be made that the investments identified were or will be profitable. The information in this post is not presented with a view to providing investment advice with respect to any security, or making any claim as to the past, current or future performance thereof.