Jeanne DeWitt Grosser, Head of Revenue & Growth (Americas) at Stripe, joined FirstMark Guilds to share how she's continued to lead Stripe's sales force, the revenue engine behind the $95B payments behemoth, through COVID with a particular focus on how she has effectively onboarded reps remotely.
What is the typical sales rep interview process? How has that changed during Covid?
The way Stripe interviews and evaluates team members hasn’t changed much during Covid. In fact, since reps are largely selling over Zoom, evaluating them over Zoom is a very natural and relevant thing to do.
Each team member goes through three stages. Importantly, every interview is highly structured, and entirely consistent across candidates. This increases efficiency, allows for more systematic improvements, and reduces bias. For the structured interview questions, Stripe has created a rubric outlining what ok, good, and great answers look like. Here are the three stages:
Stage 1: Pre-Onsite
1. Recruiter screen: Stripe recruiters are deeply embedded in functions, and
understand what the team does so they can ask 2nd-level questions.
2. Team screening: conducted by hiring manager or a senior team member,
largely focused on general team fit.
3. Homework assignment: for AEs, for example, Stripe gives potential reps a target account and ask them to present how they’d break into that account. A previous iteration was helping Stripe to develop a vertical-specific strategy.
4. Homework review: every interview Stripe conducts is highly structured; this helps you more systematically compare different candidates’ responses.
Stage 2: Onsite Interviews
Onsite interviews have obviously moved online; four interviews are conducted with the: (i) hiring manager, (ii) two team members, and (iii)one cross-functional interview.
Bonus: What kind of references do you conduct? Two of Jeanne’s favorite tactics are:
1. Great question to ask: “Stripe likes to invest heavily in training and enablement. What kind of training should we give this rep?” (A much softer and productive way of asking, “What are this person’s weaknesses?”
2. Customer interviews: asking reps to interview a previous customer gives you a totally different -- and generally much more honest -- perspective.
Stage 3: Final round
The hiring manager conducts the final round interview; and for all roles Manager and above, Jeanne conducts an interview. This round is primarily focused on final details and addressing any questions that came up in the first two rounds.
How do you onboard new reps at Stripe, especially in the Covid era?
The first week for a new hire is general in nature, and oriented around Stripe as a company. It’s an opportunity to learn the company, strategy, culture, and meet fellow Stripes across functions.
The second week is when sales-specific onboarding begins. The main topics include an orientation to the org structure as a whole, deep dive on the typical sales (customer) journey, a healthy number of product deep dives , tools training , and a *lot* of mock pitches. All of this has been formalized over time into a structured 30/60/90 day program based on function.
Bonus: new hires are assigned a “spin-up” buddy, who is typically a peer in their organization. The spin-up buddy is responsible for helping new hires in all sorts of ways: answer tough questions that haven’t been asked yet; help cement training that a new member has gone through; and to co-pilot with the new hire on any deals they are working.
What is the cadence of your performance management for sales team members?
All members of the sales team have weekly 1:1 meetings. In addition to that, Stripe has a quarterly sales kickoff meeting, where they review teamwide performance, individual performance, the next quarter’s targets and priorities, and other items like key strategic initiatives, their hiring plan, and quarterly awards.
There’s also a weekly staff meeting, and a monthly all-managers meeting. Stripe is very disciplined about forecasting, with a weekly forecasting update call, and deep dives into the forecast at quarter open, mid-quarter, a final call for the quarter, and a quarterly close post-mortem.
Stripe conducts biannual performance reviews
Bonus: once Stripe became more disciplined about managing middling performers, team performance soared. To do this, they conduct a 5-point rating system (exceeds expectations, meeting expectations, etc.) -- and for those that are at or just below expectations, they began to ask, “Would you enthusiastically rehire this person?” If the answer is no, you are likely saddling your team with lower performers. Active management of this group can help middle performers become top performers; or help you part ways with a low-performer earlier.
How is your sales team structured at Stripe?
When Jeanne joined five years ago, there were Account Executives (hunters) & Account Managers (farmers). At the time, the AMs were actually mostly support-focused with a slight commercial angle to their work.
At the time, leadership realized they needed to do more “buffalo hunting”. And the first thing Jeanne noticed is that reps were negotiating $100K deals at 9am and $10M deals at 10am - which didn’t make sense. So the first team segmentation was breaking into enterprise and mid-market.
Part and parcel of this evolution is going from single- to multi-stakeholder buyer -- and also meeting entirely new buyer personas. Selling to a technical founder/developer, which was Stripe’s original DNA, was completely different from selling to a different persona - say, a financial buyer.
The second breakpoint was vertical segmentation, followed finally by functional segmentation -- amazingly, for a technical-driven company, it was a long time before they had a sales engineer. (That’s the beauty of product-market fit.) Jeanne believes, in general, that leaders over-segment their organizations. The way she has led: evolution over re-org; as in, don’t create a segment-specific team until it’s blindingly obvious that you need a team dedicated to that segment.
How does Stripe handle the self-serve sales motion? And its named account motion?
Stripe lead-scores all inbound leads. Depending on that score, leads are sent down different nurture paths. If one has a super high score, our outbound team is tasked with getting in contact and then will flip them to an industry-focused AE.
For Enterprise, Stripe is named-account oriented and have three clear tiers (1, 2, & 3). For all Tier 1s, we have an ABM approach that’s deeply-integrated with Marketing. For Tier 2 & 3, they get more of a coverage model (e.g broad-based digital marketing/events vs. hardcore CXO roundtable type stuff for Tier 1s).
Bonus: use a campaign committee to drive sales & marketing alignment, especially on Tier 1 ABM accounts. Stripe’s campaign committee is made of the outbound sales team (including some managers), the head of demand gen, and designated leaders from marketing. The campaign committee agrees on all aspects of a sales/marketing campaign: the target, the messaging, the marketing, the sales script, and beyond.
At what size would you recommend hiring your first sales enablement lead?
Stripe shouldn’t be the best-practice here as they still only have 1 sales enablement lead for 500 salespeople. Jeanne noted that to date their strategy has been to have high-performing sales managers build out the sales curriculum, training, etc. -- however having one person dedicated to being true sales enablement, not just an athlete, is beneficial as there’s a very clear set of skills that person should have (e.g. setting up training for retention, media for diff training etc.) For context, Justworks recommends 50-75:1 for the ratio of salespeople to sales enablement leads.
What skill(s) do new salespeople most frequently lack?
There are two key deficiencies we typically see in (especially young) salespeople: the first is a lack of discovery skills. Typically, a salesperson sees one small buying sign and reads too much into it, instead of asking the right questions to really unearth the buyer’s goal. New reps need a lot of training to get comfortable asking the dozens of discovery questions they need to, and doing it over and over again with every deal.
The second is an underappreciation of the time they should spend “above the line” or with key decision-makers on any given deal. One “aha!” moment for young salespeople is to clearly articulate which personas are “above the line” vs “below the line. Below is the functional buyer (typically very easy for the salesperson to talk product with) who is very tactically oriented. Above is the strategic executive buyer, who is much more focused on long-term, strategic goals. They are very different conversations, and most early sales people don’t give enough focus to “above the line” conversations.
What’s in Stripe’s sales stack?
Some important context: “Our security ops team is fairly draconian, so our stack is somewhat basic”. Today, Stripe is using: Salesforce, SalesLoft for outbound, Troops for pumping Slack into Salesforce, Marketo, and the Lead Sprinkler plugin to round robin leads.
