Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889

Career Trajectory:

• OJ Herzberg began in equity research at Morgan Stanley before moving to venture capital at NEA, where he observed investors leveraging operating backgrounds to help founders.
• He chose a sales path after concluding that successful operators must either build or sell, viewing everything else as supportive.

Key Learnings from Dropbox:

• Shift in B2B Adoption: Technology adoption in businesses moved from top-down decision-making to a "Bring Your Own Device" (BYOD) era starting around 2010, catalyzed by the iPhone.
• BYOA Movement: Dropbox shattered traditional adoption models by pioneering "Bring Your Own Account" (BYOA), empowering employees to choose tools.
• PLG Differentiation: Product-Led Growth (PLG) represents a fundamentally different go-to-market strategy compared to traditional B2B sales motions.

Key Learnings from Asana:

• Hybrid GTM Success: Asana pioneered the simultaneous execution of Product-Led Growth and traditional enterprise sales, proving both models can coexist.
• Founder Strategy: Founders should not ignore sales teams in PLG motions; sales are necessary to handle larger, strategic conversations and move upmarket.

Playbook Philosophy:

• Definition: A true playbook is a repeatable, scalable, and cookie-cutter process, which is distinct from the initial "first playbook" of discovering product-market fit.
• Timing for Creation:
  • Founders must define the initial playbook (target persona, value proposition, messaging) before hiring, as this requires firsthand customer feedback.
  • A formal, repeatable sales playbook typically cannot be codified until after hiring at least 20 ramped Account Executives (AEs).
  • Early-stage teams should focus on agility and collecting insights rather than enforcing rigid repeatability.
• Dynamic Evolution: Founders should expect playbooks to be living documents that improve weekly, with reps tasked to bring back insights on how to make the V1 better rather than just hitting numbers.

Hiring Sequence & Strategy:

• Head of Sales vs. Reps: The choice depends on the market category:
  • Existing Categories: Hire a Head of Sales first if the category, buyer, and budget are well-defined to accelerate scaling.
  • New Categories: Hire individual reps (or customer-facing staff) first to learn the market, define the motion, and determine if to target enterprise, SMB, or specific personas.
• Timing: In the current capital-rich environment, founders should hire customer-facing staff as early as possible to gather market insights, even if immediate revenue generation isn't the primary goal.
• Batch Hiring: Hiring reps in batches is preferred to facilitate group onboarding and allow for A/B testing of approaches.

Sales Rep Traits & Interviewing:

• Core Traits:
  • Reverence for Product: Candidates must demonstrate genuine passion for the product's intricacies, not just the ability to recite a script.
  • Multiplayer Mindset: Candidates should demonstrate a track record of making colleagues better, evidenced by specific examples of mentorship or team elevation.
• Interview Structure:
  • Assess 4-5 specific competencies across multiple interviewers to reduce bias.
  • Include a prepared demo (not impromptu) to gauge potential and preparation skills.
  • Require at least one cross-functional interviewer (e.g., Product, Marketing, Recruiting) to ensure diverse perspectives.

Compensation & Equity:

• Variable Comp Caution: Implementing standard commission plans too early is risky due to lack of historical data; initial variable compensation should focus on logos, deal counts, or team bonuses rather than fixed ARR targets.
• Equity Misstep: Founders often undervalue equity for early sales hires; early sales staff are foundational to culture and product knowledge and require equity to prevent a purely transactional relationship.

Onboarding Process:

• Sequence:
  1. Support Exposure: First, handle support tickets to understand common product issues and "gotchas" before learning sales scripts.
  2. Market Knowledge: Review fundraising decks and competitive landscapes to understand the broader ecosystem.
  3. Sales & Shadowing: Shadow founders on customer calls and learn value articulation.
• Certification: The process concludes with a high-stakes, role-played product demo to "defend their thesis" before speaking to customers.
• Timeline: Approximately two months for full certification; PLG companies may allow customer interaction (non-selling) as early as three weeks.

Scaling & Outbound Strategy:

• PLG Plateau Warning: Founders should not immediately pivot to outbound when inbound PLG plateaus, as outbound requires different personas, messaging, and higher deal sizes.
• Preparation for Outbound: Effective outbound requires a company-wide initiative to align marketing and product for senior personas; simply buying lists and cold-emailing rarely works.
• Diversification: Companies should begin layering outbound strategies before the inbound funnel fully plateaus rather than treating it as a last resort.

CEO & Head of Sales Relationship:

• Partnership Dynamic: The Head of Sales must act as a strategic partner to the CEO, providing filtered, unbiased feedback to aid decision-making.
• Meeting Cadence: Weekly meetings are essential in early stages to prevent recency bias and ensure the CEO receives high-quality market data.
• Post-Mortem Rigor: Use frameworks like the "Five Whys" (from Toyota) to move past surface-level excuses (e.g., "bad timing") to identify root causes like lack of training or prioritization systems.

Fast-Fire Insights:

• Enduring Tactic: Articulating business impact and value remains the most critical sales tactic of the last five years.
• Dying Tactic: Cold email blasts and relying on marketing automation metrics (like white paper downloads) to generate leads are largely ineffective.
• Common Founder Mistake: Failing to invest in the feedback loop between customer-facing teams and product teams.
• Advice for New Sales Leaders: The primary challenge is "managing up" to ensure clear dialogue with founders and boards to align on progress against high valuations.
• Ideal Industry Shift: Sales culture needs to shed the "used car salesman" stereotype and be recognized as equal partners to product in solving customer problems.