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I chatted with this big-time VC, and he’s hyped on this one startup pulling all the top talent: Ramp. If you don’t know, they do biz cards and help with spending. They’re worth $8B+, backed by Founders Fund, Stripe, and more. Grew 4x last year to $10B+ in spending. Fastest-growing SaaS ever—hit $100M in 2 years. I am not an investor, but man, I wish I was.

1. How far ahead do you plan, and how has that changed?

At Ramp, we’re all about speed. It’s in our vibe, our teams, how we grow, and how we fix stuff. Speed isn’t just a flex; it’s how we help our customers save their squad’s time and cash.

Our planning is built for speed. We think doing > planning. Every second spent planning is a second not doing. We don't sweat the fine print once we’re set on a path. Trying to predict the future? Nah, too pricey and pointless. We just stay quick, learn daily, and adjust fast. Over time, our mix of planning and doing has shifted, but we’re still big on action:

Pre-PMF, tiny team (<20): It was all about finding PMF when I joined. Had a ton of ideas, but the move was to lock in on one thing and crush it. Two-week sprints were the sweet spot. No long-term plans. It was, “What’s today’s grind? What’s this week’s goal?”

PMF locked, core card lit, 100+ team: We leveled up to plan for one or two quarters in months. We needed more sync with sales, marketing, and ops—teams that need longer cycles. Tech shifted, too, focusing on reusable, solid systems for future vibes.

Multiple products, big squad (500+): Now we’re playing in the big leagues. Solid core biz, new products, and big plans to scale. Longer sales cycles and big GTM moves mean quarterly plans. But hey, if the plan sucks by the time it’s done, we chuck it and keep rolling.

2. Y’all vibe with OKRs?

Here’s the tea: folks start with OKRs, but real talk—they should kick off with strategy. OKRs feel kinda sus like you’re reverse-engineering goals just to fit the framework. You’re sweating over words and metrics, stressing if teams will get judged on ‘em. You tweak and tweak, and guess what? The plan barely shifts.

To slay the market, be product-strategy-core, not sales or hype-led. Bet on your product to serve customers, ‘cause that’s what brings the bag for your biz. This mindset? Gotta build it early.

Here’s how we roll:

1. Start with the vibe: product strategy, bottom-up. Know what you wanna do and why it’ll hit diff for your crew and biz. Pods run their roadmaps, bottom-up style. First, we lock in the product dream and top 2-3 squad goals. Then, we let the homies closest to the probs map their moves. Together, we co-create the big start.

Here’s how we break it down:

1. Goal → What’s the glow-up you wanna see?

2. Hypothesis → Why will this pop off?

3. Right to Win → Why us? What’s our edge?

4. Metric → How do we prove it’s slayin’?

5. Initiatives → What steps to get the dub?

6. Risks → What could flop & how to dodge it?

7. Long-Term Outcomes → How will this keep paying off?

Peep the template for the whole play.

2. Lock the product and start the money game. If your plan isn’t tied to how the business bags cash, it’s doomed. Always peep how we make the bank and balance the vibes between new stuff, growth, and cash flow. For example, in one quarter, we might chase margins, cut credit losses, or drop new revenue streams—we sync all that with finance.

3. Drop the roadmap and sync it to the marketing hype. We share a top-line plan, get squad feedback, and make sure it vibes with the big marketing moves we’re cooking. This way, our product drops hit louder. Planning isn’t just goals—it’s trade-offs. Everyone wants it all, but nah, that’s not real. By calling out trade-offs, we can chop it up over X vs. Y instead of "all the things." Example:"

4. Set high-level OKRs to get squads moving as one. Don’t drag it out—keep it quick. We noticed that we were spending one month each quarter just on planning—like 33% of our time. So, we switched to planning twice a year and made it all about the big stuff, not a list of every team’s tasks.

   The goal? Make tough calls—they have to sting. Not everything on the roadmap needs to be in the OKRs. We keep it tight: just a few major cross-team projects or drops.

   Here’s the template, all filled out:

5. OKRs ≠ performance checks. Teams get judged their way. Like, sales? It’s all about hitting quotas and closing deals. Support? They’re on “solves per hour” and happy customers. None of that belongs in OKRs.

   At Ramp, we track everything with scorecards, but OKRs are for leveling up, not just holding the line. Hitting these goals takes squad collabs—eng, product, marketing, sales, all vibing together.

   Missing a goal doesn’t mean everyone flopped. You gotta dig way deeper to figure out what’s up when things don’t hit.

3. How do our product/design jams go down?

At Ramp, we keep it open. Teams make moves fast, so every spec, design, and call gets dropped in Slack. Anyone can peep and chime in—no gatekeeping here. The goal? Farm for feedback, not a thumbs-up.

Back when we were under 100 peeps, I could read it all and drop takes on the fly. But as we grew, three things went haywire:

1. Too many teams, and too much noise—I needed teams to sum up the vibes and key moves.

2. Senior PMs have more trust—They have more autonomy to choose when to loop me in.

3. Mixed signals—Design and product weren’t always synced, and it slowed us down.

Now, for big calls or risky moves, PMs hit us up at the weekly product jam (Wed, 4 p.m.). This sesh is all about speed, context, and squad sync:

• Focus on what matters—New stuff or major UX shifts. PMs ask: If we botch this, will it wreck our goals? If yes, bring it. If not, skip it.

• Stay fast—It’s lightweight. Just sign up and roll through.

• Align product + design—Both leads are in the room, so no mixed takes.

• Keep it tight—Only the eng leads join. Other voices? Should’ve been looped in at the spec stage.

The process is like the product—it’s a WIP. We’re always tweaking the flow.

4. Are products and designs in one squad? Who do PMs vibe with? Has it changed?

The key to speed? Build your squads so they have to collab:

• PM, Design, Eng, Data = Equal partners. Always been the vibe. If design reports to the Product, UX takes the L. Design needs its flow to drop big-brain ideas.

• One boss, tech-first. At Ramp, we all report to the CTO. If the Product goes to the CEO and Eng to the CTO, it gets messy. You don’t want Product as "stakeholders" to Eng—they should be co-creators.

• You ship your org. Build your squad like you want your product to work. If Data isn’t equal, you’re losing the power of facts, data-driven calls, and real accountability. As you grow, this matters big time.

4. Are products and designs in one squad? Who do PMs vibe with? Has it changed?

The key to speed? Build your squads so they have to collab:

• PM, Design, Eng, Data = Equal partners. Always been the vibe. If design reports to the Product, UX takes the L. Design needs its flow to drop big-brain ideas.

• One boss, tech-first. At Ramp, we all report to the CTO. If the Product goes to the CEO and Eng to the CTO, it gets messy. You don’t want Product as "stakeholders" to Eng—they should be co-creators.

• You ship your org. Build your squad like you want your product to work. If Data isn’t equal, you’re losing the power of facts, data-driven calls, and real accountability. As you grow, this matters big time.

5. How do we squad up? Has it changed?

Squad vibes impact speed, and here’s how we roll at Ramp:

• Outcomes > Everything. Squads own big moves that matter. It fires them up. Like:

  • “Drive 50% of sales leads with outbound emails in 3 months.” Boom—done.

  • “Build a Bill.com rival in 3 months.” Crushed it.
    Big goals, tight clocks, and no blockers = magic. But squads must know how the biz runs.

• Squads post their ‘why.’ Every squad shares their purpose loud and clear:

  • Goal: What’s the aim?

  • Strategy: How’ll they slay?

  • Roadmap: What are they building?

  • Metrics: How is success measured?

  • User Flows: What’s the UX?

  • Systems: What tech runs it?

  • Stakeholders: Who do they vibe with?

This setup keeps us sharp, synced, and sprinting.

Make staffing flex.

Speed wins, so we keep squads flexible. Folks can jump pods based on the biz vibe, even if they report to different leads. Managers handle hires, coaching, and growth, while Tech Leads drive strategy and do the thing. Reporting stays steady—pods shuffle. This way, we grab new chances without breaking bonds.

Embed platform squads, but not forever.

Platform squads need biz vibes to move right and fast. We keep them in core pods for as long as it works:

• Payments platform? With Bill Pay. Most use cases = B2B payments.

• Data science? With Risk. Most needs = underwriting.

Once they rack up wins, we spin them out to collaborate across pods.

Small squads = fast moves.

We keep pods tight—5 to 10 eng max. Like with Bill Pay:

• Started as one pod.

• Grew into four sub-pods.

• Spun one out to own workflows across Ramp.

Map the squad to the biz goals.

Single-threaded squads + all the tools = speed. Every pod links product goals to biz goals. Each one gets:

• Product Marketer

• Product Operator

• Partnerships Lead

• Product Counsel

These peeps QB the start in their zones, keeping it all locked in.

6. How many PMs?

We’ve got 14 PMs now (btw, we’re hiring 🫡).

Ramp’s vibe: max leverage = big wins / small squads. For the first 2 yrs, we had <5 PMs + <50 engs and still hit $100M ARR. We only hire PMs when it’s so clear that Product is the blocker. Why?

• Everyone learns PM vibes. Folks care more about biz goals, pain points, and shipping.

• Big scopes = no drama. PMs are too busy crushing it to fight over resources.

• New PMs = instant love. When a PM joins, the team’s hyped. They need them, and the PM gets early dubs.

What makes Ramp’s product game strong:

• Speed kills. Always chasing velocity.

• Dope framework. Their product strat template slaps.

• Tied to $$$. Product plans = synced with the bag.

• Planning evolution. From 2-week sprints to 6-mo plans with deep Q roadmaps.

• Tiny squads, big moves. <5 PMs + 50 engs = $100M ARR.

• Outcome squads. Pods built for biz goals (e.g., bill pay attach rate).

• One tech boss. PM, design, eng = all report to CTO.

• First-principles mindset. Think fresh, no copy-paste.

• Smart hires. ICs > managers, all day.

Ramp = the blueprint. 🚀

What I found amazing this week

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This track gave me a serious boost—check out ‘Back Home’ by Gold Panda🎵

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