CEO, Highland & Haskill Creek • Founder of Classy (acq. by GoFundMe) • Founder of nonprofit, Save Farmland

Every week I tackle management, operations & startup topics that are helping 250,000+ people. Sign up free: www.scotchisholm.com

I also run a leadership accelerator that helps founders develop into top CEOs. Apply here: https://joinhighland.com/apply/

My backstory: 

🚀 Founder of Classy, SaaS for nonprofits raising billions per year

🎗️ Acquired by GoFundMe in ‘22 to create largest giving platform in the world

🌲 Investor in dozens of startups out of family fund, Tall Timbers Holding Co, (Ripple, FanDuel, Hubble, Casetext, etc.)

🏔️ Founder of Highland, leadership accelerator & community for founders

🏡 Co-founder of Haskill Creek, modernized & healthier version of a Walgreens or CVS 

⚽️ Co-owner of Albion Soccer Club, top youth soccer club in country

🧑🏼‍🌾 Founder of Save Farmland, a nonprofit protecting local farmland & food 

⚙️ Industrial engineer & lean six sigma nerd, UMass Amherst grad 

❤️ Board experience: Nature Conservancy, Abundant Montana, Team Rubicon, Street Soccer USA, Montana Pediatric Cancer Foundation

It's been a wild ride. If you're interested in any of the above, please visit my website and reach out to me there. 

www.scotchisholm.com

Scot Chisholm

I've spent two decades building the operational infrastructure that allows venture-backed startups to scale without breaking.
I've architected people strategies, yes—but I've also run finance, launched entities across continents, led post-merger integrations, and sat in the room where growth, cash, and culture collide. That's the nature of startup operations: you don't get the luxury of a narrow mandate. You build what's needed, when it's needed, with an entrepreneurial mind and an operator's rigor.
I've managed dual P&Ls across US and European entities, navigating intercompany accounting, transfer pricing, multi-currency reporting, and VAT compliance across jurisdictions. I've set up legal entities, overseen monthly closes, directed comprehensive financial operations while building people functions from scratch. I've scaled companies from $500K to $12M ARR, from 7 to 350+ employees, across 12 countries and seven time zones—through bootstrapped growth and venture-backed hypergrowth.
I've worked across SaaS, DataOps, cybersecurity, and AI—all B2B, all high-growth. I've been HRBP to leadership teams, led companies through reorganizations, acquisition integration (92% key talent retention), and funding rounds. I've implemented financial controls, built HR tech stacks, and created the systems that allow distributed teams to function as one company.
Here's what that looks like in practice: workforce planning modeled against revenue milestones and burn rate. Compensation frameworks that treat equity and cash as levers, balancing fairness across geographies with cap table reality. Performance systems that make the connection between daily work and quarterly OKRs legible, so people know why their work matters and leaders know where to intervene. M&A integration that preserves the value you bought while converging operations—without losing the talent that made the deal worth doing. And the operating cadence—standing meetings, decision frameworks, feedback loops, rituals—that substitute for hallway serendipity when teams span time zones. It's the scaffolding that lets companies adapt without eroding trust.
Whether the role is Chief People Officer or the broader operational leadership that early-stage companies require, I bring cross-functional fluency, financial literacy, and two decades in the engine room of venture-backed growth. As an ICF-certified Executive & Organizational Development Coach, I work with founders stepping into the CEO role and leaders inheriting new scopes—because building systems is one thing, developing the leaders who run them is another.

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Scot Chisholm

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