How a 25-Person Fintech Startup Built Their First Sales Playbook

Details shared with permission.

Situation

A fintech startup with 25 employees had raised a Series A and needed to scale sales beyond the two co-founders who had closed all initial deals. They hired 3 account executives but after 4 months, none had closed a deal. The board was asking questions about sales execution.

What was unclear

The co-founders sold through personal networks, industry events, and warm introductions. This approach could not be replicated by new hires who did not have the same relationships or industry credibility. There was no documented sales process, no call scripts, no objection handling guides, and no clear handoff from marketing to sales.

What we changed in the system

We documented the co-founders' sales approach through structured interviews and deal retrospectives. We identified the 5 most common buyer objections and created evidence-based responses. We built a complete sales playbook covering prospecting, discovery, demo, proposal, and negotiation stages. We created a 30-60-90 day plan for new AEs with specific milestones and KPIs. We set up a deal coaching rhythm where co-founders reviewed pipeline weekly with the team.

What improved

Two of the three AEs closed their first deals within 6 weeks of the playbook launch. The team collectively generated $450K in new ARR in the following quarter. Ramp time for new hires dropped from an estimated 6 months to under 90 days. The co-founders reduced their direct selling time by 70%, allowing them to focus on product and fundraising.

Go deeper

Read the thinking behind our approach, learn how we work with teams, or start a conversation about your situation.

Deal Stage Distribution (After Playbook)

Playbook Impact

after	before	metric
2 weeks	8 weeks	Onboarding Time for New Rep
22%	8%	Win Rate
$28K	$15K	Avg Deal Size
High	Low	Forecast Accuracy

Explore further

Facing a similar challenge? We'd be happy to discuss your situation.

Start a conversation