How Sarah Tavel Evaluates Startups: From Pinterest PM to Benchmark GP

General
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Sarah Tavel’s journey from venture analyst to Pinterest’s first PM to Benchmark General Partner gives her a unique perspective on evaluating startups. Here’s what we can learn from her investment philosophy.

The Conviction-Driven Approach

When Tavel invested in Pinterest’s Series A at Bessemer, she described it as:

“There was something from the very beginning where I felt like this was the product. It was one of those, ‘this is it’ convictions.”

This conviction was so strong that she left venture capital to join Pinterest as a PM—a rare move that deepened her operating experience.

Operating Experience as an Edge

Having been a PM at Pinterest during hypergrowth, Tavel brings operator empathy to investing:

“One, you have an immediate level of empathy for the founders because it’s so freaking hard. Two, I’m much more interested than I used to be in the thought process that got to the metric they’re focused on today because that reflects how they’re running their company.”

She looks beyond the metrics to understand the reasoning that led to those choices.

Market vs. Team

Tavel agrees with Andy Rachliffe’s view that market often trumps team:

“Founders are critical in the initial assessment, but market dynamics are decisive. Markets are dynamic and influenced by technology and trends. The best investments are often a combination of great founders and evolving markets.”

She looks for small markets adjacent to very large ones—opportunities that look niche today but have expansion potential.

What She Looks For

Based on her public comments, Tavel evaluates:

  1. 10x product that’s also cheaper than alternatives
  2. Network effects or competitive moats that compound over time
  3. Core action clarity—does the founder understand their product’s essence?
  4. Path through the Hierarchy of Engagement—can they achieve all three levels?
  5. Market timing—is technology or behavior shifting to enable this?

Investment Focus Areas

At Benchmark, Tavel focuses on:

  • Consumer businesses and marketplaces
  • Consumerization of IT
  • Crypto/web3 ecosystem (Chainalysis, Sorare)

She’s notably not focused on crypto at the protocol level—she cares about consumer experience.

Benchmark’s Unique Structure

Tavel attributes success partly to Benchmark’s structure:

“Benchmark’s structure as a very small, intimate, equal partnership.”

Unlike most firms, Benchmark divides management fees and carry equally among GPs. Each GP leads just 1-2 deals per year, enabling deep involvement with portfolio companies.

The First Female GP

Tavel joined Benchmark as the first female GP in the firm’s history. She’s also a founding member of All Raise, the nonprofit accelerating women’s success in VC and startups.

Key Takeaway

Tavel’s approach combines:

  • Deep product intuition from operating experience
  • Framework-driven evaluation (Hierarchy of Engagement, 10x + cheaper)
  • Conviction-based decisions with high concentration

What aspects of her investment philosophy resonate with you? For founders: what signals do you think matter most to investors like Tavel?

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Tavel’s career path is fascinating for anyone trying to break into VC. Let me map it out:

The Path: Analyst → Operator → GP

  1. Bessemer Analyst (entry-level) → VP (rose through ranks)
  2. Pinterest PM (3+ years operating at hypergrowth)
  3. Greylock GP (returned to VC with operating cred)
  4. Benchmark GP (joined the most prestigious early-stage firm)

Key Lessons for Aspiring VCs

Operating Experience Matters More Than Ever

The “2 and 20” model works when you add real value to portfolio companies. Operating experience gives you:

  • Pattern recognition from inside a scaling company
  • Credibility when advising founders
  • Empathy that founders can sense

Conviction Requires Domain Expertise

Tavel’s Pinterest conviction came from deeply understanding the product category. She wasn’t just looking at metrics—she felt it was the product.

Implication: If you want to invest in a space, you need to really know it. Surface-level research won’t generate conviction.

The Cold Email Still Works

Tavel found Chainalysis through a cold email tip from Katie Haun. She then cold-emailed the founder. Even top-tier VCs are sourcing deals through network and hustle.

Concentration > Diversification (at Benchmark)

Benchmark’s model of 1-2 deals per GP per year is the opposite of spray-and-pray. This requires:

  • Very high conviction
  • Saying no to 99%+ of deals
  • Deep involvement with few companies

Questions I’m Wrestling With

  1. Is the operator-to-VC path becoming table stakes? Will pure finance backgrounds be disadvantaged?
  2. How do you develop conviction without operating experience? Is pattern matching from many deals a substitute?
  3. Benchmark’s equal partnership seems rare—do other structures create misaligned incentives?

For those in VC or trying to break in: what’s your take on the operator-to-investor path?

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As a founder currently fundraising, here’s what I take away about what to look for in an investor like Tavel:

What Founders Should Look For

1. Do They Understand Your Business Deeply?

Tavel mentions she’s “more interested in the thought process that got to the metric” than the metric itself. This means:

  • Good investors ask “why” not just “what”
  • They probe your reasoning, not just your numbers
  • They want to understand how you think

Red flag: Investors who only ask about growth rate and don’t dig into product decisions.

2. Operating Experience in Your Domain

An investor who’s been a PM at a consumer company will give different (often better) advice than one who’s only seen companies from the board seat.

Questions to ask investors:

  • “What’s the hardest product decision you’ve personally made?”
  • “When have you been wrong about a market?”

3. Conviction Over Consensus

Tavel talks about “this is it” conviction. You want investors who believe in your specific vision, not ones who are hedging across 50 similar bets.

Signs of conviction:

  • They lead the round (not just follow)
  • They move quickly after diligence
  • They have a clear thesis for why you’ll win

4. Time and Attention

Benchmark’s 1-2 deals per GP per year means their companies get real attention. Many firms have GPs juggling 10-15 active boards.

Ask: “How many boards are you currently on? How much time do you spend with each company?”

The Flip Side: Are You Investor-Ready?

Tavel’s frameworks give you a checklist:

  • Can you articulate your core action clearly?
  • What’s your path to Level 3 (network effects/virtuous loops)?
  • Are you 10x better AND cheaper than alternatives?
  • What’s your accruing benefits and mounting losses story?

If you can’t answer these, you’re probably not ready for a Benchmark-tier investor.

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Important to highlight Tavel’s role in All Raise and what it means for the ecosystem.

The Numbers Problem

When Tavel joined Benchmark, she was their first female GP—in a firm founded in 1995. That’s over 20 years with an all-male partnership at one of the most influential VC firms.

And Benchmark is far from the worst. As of recent data:

  • ~15% of VC partners are women
  • ~2% of VC funding goes to female-only founder teams
  • ~20% goes to mixed-gender teams

Why All Raise Matters

All Raise, which Tavel co-founded, works on both sides of the table:

For VCs

  • Training and mentorship for women rising through VC ranks
  • Visibility for female investors
  • Accountability metrics

For Founders

  • Connecting female founders with investors
  • Workshops on fundraising and scaling
  • Community support

Why Diversity Improves Returns

This isn’t just about fairness—there’s an alpha argument:

  1. Untapped deal flow: Female founders are less likely to have warm intros to male VCs. Female VCs access differentiated deal flow.

  2. Different pattern matching: Homogeneous partnerships miss opportunities that don’t fit their mental models. Pinterest’s appeal might be more obvious to someone who uses it.

  3. Better decisions: Diverse groups make better predictions than homogeneous ones (research consistently shows this).

What Founders Can Do

  • Explicitly seek out female investors (check All Raise’s database)
  • Support female-founded startups as customers/partners
  • Share cap tables—transparency helps

What’s Changed?

The conversation has shifted from “is this a problem?” to “how do we fix it?” But progress is slow. Having Tavel at Benchmark is symbolically huge, but we need systemic change, not just exceptional individuals breaking through.

For female founders: what’s been your experience fundraising? For VCs: what’s your firm doing differently?