💫 Ramplify: October Observer

Product at scale? Vibe Coding Peak? Build with intuition.

(Rampersand’s Taryn Pieterse, Culture Amp’s Rod Hamilton, Restoke Co-Founder Ken Brand, Cake Equity Senior Product Manager Aaron Blakemore)

🚀 Aligning Product during Hyperscale! By Taryn Pieterse

If you are a product-centric founder or builder, we have some exciting product-focused events coming up this November. If you’d like to be added to the invitation list, please express your interest here.

At the SaaS Summit in Melbourne last week, I sat down with three product leaders who have navigated this exact challenge: Rod Hamilton (co-founder and former CPO at Culture Amp, Venture Partner at Rampersand), Ken Brand (co-founder and CTO at Restoke.ai), and Aaron Blakemore (Senior Product Manager at Cake Equity). Whilst each is at a different stage of growth, all have wrestled with the same fundamental question: how do you keep the product team and priorities aligned when everything is moving at breakneck speed?

The conversation revealed that alignment isn’t just about having the right processes or perfect communication; it’s also about having the right mindset. It’s about something much more visceral.

The Swagger Test

Rod put it perfectly when describing how you know your product team is truly aligned:

“It’s when you see swagger across the org. It’s swagger in your sales team in how they talk about the product. It’s swagger in your customer success team when they talk to customers, even when there’s bad stuff happening in the product, they’re really confident in it.”

In hyper-growth environments, perfect alignment is a myth. What matters is whether your team feels collectively invested in solving the complex problems together.

Signal vs. Noise in the Age of Everything

Every product leader faces the same nightmare: too much data, too many customer requests, too many “urgent” priorities. Ken shared how they use AI to analyse every customer conversation, but noted something crucial:

“Everyone’s feeling that they need to back their product request with data. If they have a customer they really want to close or there is something that customer really needs, they have to come up with 10 more customers that actually want the same thing to be able to prove it.”

The discipline isn’t just in collecting data – it’s in demonstrating true and widespread demand from customers.

Aaron’s observation is that when people chase the noise, they become “headless chickens.” He notes that true signals often come from the slow burns - the metrics that have been quietly trending upward for months.

Selling The Roadmap

There is always tension between the sales team and the roadmap of features to be delivered. Rod utilised the “666 roadmap” framework, which is brilliant for aligning Product and Sales. Be clear and aligned on the next six weeks of high-confidence delivery, six months of problem-focused direction, and six years of vision.

Aaron has taken this further, actively selling features before they’re built – but with the discipline to only commit to the build when they can quantify the ROI upfront. It’s a high-risk, high-reward approach that only works when you have deep conviction about your product direction.

The Takeaway

The key takeaway for building successful product teams, as combined by Rod, Ken, and Aaron, is to continuously reinforce the roadmap and ensure the team stays aligned and motivated around the mission.

If you’re building in a product-centric way, we’d love to hear from you.

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🗞️ Tech News:

dbt Labs and Fivetran to merge: the modern data stack bundles — ELT meets transformation in one house: Fivetran (data movement/connectors) and dbt Labs (analytics engineering/control plane) are combining in an all-stock deal, with Fivetran CEO George Fraser slated to lead the merged company and dbt founder Tristan Handy to become president. The goal: shorten time-to-value for analytics and AI by collapsing ingest → model → govern into a single platform.

“The combined entity would have one of the strongest platforms for preparing enterprise data for analytics and AI.”

Vibe Coding Peak? The tweet suggests that coding may have peaked, but the founder of Lovable denies the data. However, it's interesting to think through the implications for the startup landscape.

Gemini Enterprise: Google’s new ‘front door’ for AI at work — Google unveiled Gemini Enterprise, a consolidated, agentic platform where employees can chat with company docs, data and apps and build/deploy AI agents (with governance) in one place. Plans start from business tiers around $21–$30 per user/month, and Google positions it as the central workspace to automate workflows across tools and data sources.

OpenAI moves to the automation app layer by launching a no-code Agent Builder — A visual canvas to build multi-step AI agents (no code), then ship them with an embeddable ChatKit UI, built-in guardrails, and first-class evals. Under the hood, it pairs with the Agents SDK (Node/Python/Go) and the Responses API, cutting “glue code” and helping teams move prototypes to production faster.

“With Agent Builder, you can drag and drop nodes, connect tools, and publish your agentic workflows with ChatKit and the Agents SDK.”

Joshua Kushner & Thrive: Building by intuition in “The New World” — A deep profile of Thrive Capital and founder Joshua Kushner, tracing how his personal history, aesthetic instincts, and willingness to lean into intuition shaped one of today’s most consequential VC firms. Starting with small bets on Instagram, Spotify and GitHub, Thrive’s approach emphasises conviction (something we love at Rampersand), pattern recognition, and trusting gut over convention.

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🛠️ How to Startup:

Use Your Gut: Building What Customers Don’t Know They Need —
Boldstart Ventures’ Ed Sim reminds founders that customer feedback isn’t the same as customer vision. Too many enterprise founders anchor their pitch on “what 30 CIOs told us,” but the most significant breakthroughs come from intuition and building what customers don’t yet know to ask for.

Sim draws inspiration from Jeff Bezos, who famously said:

“You should ask your customers — but it’s not sufficient. You also have to invent on their behalf because the biggest breakthroughs, the most important ideas, customers don’t know to ask; they don’t know to ask for those things. That’s why you have to dream, and you have to use your intuition and your gut and your heart.”

Five practices to strengthen your co-founder relationship — First Round Review outlines five essential rituals for co-founder harmony:

1. Weekly retrospective check-ins (gratitude + challenges)

2. “Vision alignment sessions” every 3–6 months

3. A shared “survival document” spelling out fallback roles, equity, and exit plans

4. Decision heuristics (e.g. “fast breakable bets” vs. “reserved bets”)

5. Conflict rules: when to escalate to a coach/facilitator

These small practices reduce drift, avoid unspoken resentments, and keep you aligned when the startup gets messy.

“The startup is going to test your partnership more than you think — you don’t need drama, you need structure.”

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👕 VC in Australia/New Zealand:

Cut Through Quarterly (Q3 2025) is live — Q3 tallied just over $1B across 116 rounds, the biggest quarter of 2025 by deal count. The lift came from breadth (accelerators and early-stage investments) rather than mega-rounds, with only one $100M+ deal; valuations continued to edge higher—especially at the early-stage end. *while the Series B bottleneck lingered and deep-tech (hardware/biotech) led big cheques.

“Valuations [are] rising across every stage, especially at the early end of the market… The centre of gravity has shifted up, but capital remains selective.”

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🤩 Portfolio News

Restoke launches Enterprise: the AI-powered restaurant system for scale —
The first AI platform explicitly built for multi-site hospitality operators. Designed for restaurants growing from a few venues to full-scale groups, it centralises inventory, production, team management, and commissary operations into one unified system. Unlike traditional management software, Restoke Enterprise’s AI goes beyond tracking. It forecasts sales, COGS, and production trends, surfacing insights that guide operators toward tighter margins and smoother scaling.

“Early customers report 5–7% lower COGS and seven-figure savings within months, proving that intelligent automation isn’t just for tech companies — it’s the new backbone of restaurant growth.”

Mass Dynamics Expands to North America with Key US Hire. Appointing Jennifer D’Angelo as Business Development Lead, North America, marks a significant step in its global expansion and deepening of partnerships in the proteomics space. Jennifer brings a hybrid background in genomics, proteomics, and metabolomics, combining technical expertise with commercial acumen. Her mission: to help scale Mass Dynamics’ growing community and unlock new collaboration opportunities across the US scientific ecosystem.

Matrak expands to UK as European demand grows — Melbourne-based automation & integration startup Matrak opened a London hub in response to rising demand from UK and EU clients. Their API orchestration platform will target regulated sectors there, while remaining focused on addressable automation stacks across ANZ & EMEA. The move signifies that many SaaS startups will need a physical presence to sell compliance-heavy infrastructure in the European market.

Hatch: Gen Z actually want to be in the office — Contrary to popular belief, Startup Daily interviews show that many Gen Z employees say they prefer hybrid or nearby coworking, citing social energy, better learning, more precise feedback, and simpler work-life separation. Startups hiring Gen Z should reconsider fully remote models and consider designing micro hubs, implementing rotational in-office days, and incorporating live collaboration rituals to retain early-career talent.

Functionly launches OrgPilot AI — “Cursor meets McKinsey” for org design — Org chart tooling startup Functionly released OrgPilot AI, an AI-powered planner that lets leaders type in role changes, reorg scenarios or projection models in plain English, and instantly see impact on spans, headcount, cost, and role overlap. They’re also incubating agentic org charts where roles may combine human + AI tasks, helping teams imagine future workforce mixes.

“With OrgPilot AI, you can make bulk structural changes in plain English, then see the impact in seconds.”

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💼 Portfolio Job Board

Sales Development Representative at Dexibit

• Location & type: Auckland, New Zealand (Hybrid), Full-time

• What they do: Dexibit is a data intelligence platform that helps visitor attractions and entertainment venues optimise operations through data aggregation, predictive analytics, and reporting tools.

• What you’ll do: Research, identify, and engage prospective customers in the visitor attractions sector, using multi-channel outreach and inbound follow-up to book discovery and demo meetings. You’ll maintain CRM data, refine sales methods with insights, and share customer needs with the product team while driving pipeline growth for Dexibit’s SaaS platform.

Senior Principal Solutions Architect at Skedulo

• Location & Type: San Francisco, California (Remote) & full-time

• What they do: Skedulo creates cloud-based software to allow any company in any industry to schedule, manage, engage, and analyse their deskless workforce.

• What you’ll do: Design and deliver innovative, scalable solutions for enterprise customers, lead complex implementations, and act as a trusted technical advisor to ensure maximum value from the Skedulo platform.

Do you have a job you’d like us to promote? Add it to Hatch and share the link with us.

See all jobs across the Rampersand Portfolio.

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🌏 Rampersand Travel Diary:

Andrew will be in Brisbane the week of October 27. Reach out for coffee.

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🎉 Upcoming Events

OCTOBER 21 - MELBOURNE: But first, COFFEE: Surviving the attention apocalypse, Melbourne. A punchy morning meetup (8:30–10:00 am AEDT, SleevesUp, Cremorne) on cutting through the noise: what replaces the old GTM playbook, when to hire marketing, and how to use AI to ship creative at founder speed. With Jack White (Cuttable) and Tim Farmer (DiDi). Only a handful of spots left.

OCTOBER 13-19 - SYDNEY: SXSW Sydney. Catch partner Taryn Pieterse on Day 4 at 10:00 am for the SXSW Mentoring - Join Taryn and others for a mentoring session at SXSW. More details here.

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Thanks for being part of the Rampersand Community! You can stay updated with even more news and info on our LinkedIn and X/Twitter pages.

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