Sales Leader Playbook
From founder sales to sales machine
Who This Is For
Founders doing sales, first sales hires, sales managers
Seed to Series B
You're building or scaling a sales function
The biggest mistake in sales hiring is hiring reps before you have a repeatable sales motion. Founders should close the first deals, document what works, then hire people to scale it.
1. Founder-Led Sales
Founders should do the first 10-20 deals themselves to understand the sales motion.
Founder Sales
The primary competitor in B2B sales is often customer indecision and the fear of making a high-stake...
View Skill → →Conducting User Interviews
Observational research reveals 'orthogonal' problems that are invisible in data funnels.
View Skill → →Positioning & Messaging
Using hyper-specific details in messaging helps define the problem space and differentiates the prod...
View Skill → →2. Document the Playbook
Before hiring, codify what works so you can teach it.
Sales Qualification
The guest explicitly states that most sales problems are actually qualification problems and provide...
View Skill → →Competitive Analysis
Competitive 'War Gaming' distributes market research across the team, ensuring deep immersion into c...
View Skill → →Pricing Strategy
Shifting to a direct-to-consumer subscription model requires building a 'destination-first' approach...
View Skill → →3. Build the Team
Hire people who can follow the playbook, then improve it.
Building Sales Team
Early sales hires in a PLG company should match the current inbound motion and the specific target b...
View Skill → →Evaluating Candidates
Hire for team balance and complementary skills rather than searching for a single candidate who exce...
View Skill → →Sales Compensation Design
The guest provides specific tactical advice on OTE ratios, base/bonus splits, and ramping strategies...
View Skill → →4. Go Enterprise
Enterprise deals are different—longer, more stakeholders, higher stakes.
Enterprise Sales
Enterprise sales require a high-level narrative to align diverse stakeholders within a buying commit...
View Skill → →Stakeholder Alignment
Growth leaders must bridge the gap between rapid experimentation and product craftsmanship to gain o...
View Skill → →Partnership & BD
Securing strategic partnerships with major platforms (like Facebook or Google) requires demonstratin...
View Skill → →Common Mistakes to Avoid
- Hiring a VP of Sales before you have repeatable revenue
- Letting sales drive product roadmap
- Discounting your way to revenue
- Hiring expensive enterprise reps for SMB deals
- Not tracking why you lose deals