The Operator 1 - Harry Siggins shares his Chief of Staff journey growing Quantive from 20 to 400 people.
Harry Siggins was one of the early hires at OKR-SaaS startup Quantive. In this issue, we discuss the evolving Chief of Staff role, making OKRs work, and share advice for breaking into this role.
Harry’s path to a Chief of Staff role
Harry initially didn’t plan to become a Chief of Staff. What drove him wasn’t solving one specific problem or working in one industry - it was thinking in terms of systems and improving execution.
After starting in a technical management consulting role, he craved a more dynamic environment. He ended up working at Techstars in Berlin and met the founder of GTMHub (now Quantive).
"I was much more about how I can plug and play — and use my skills to help facilitate company growth."
Harry joined the company and, as one of the first US hires on the team, started out building the Customer Success function as Quantive was driving US-expansion. Through solving customer issues, building operations from the ground up, and launching the US Go-To-Market strategy, Harry transitioned into a Chief of Staff role.
Inside Harry's Chief of Staff Journey: Scaling at Startup Speed
When Harry joined Quantive, the company was a 20-person startup that had just raised their seed round. Over the next five years, he witnessed - and helped drive - the company’s growth past 400 employees all the way until the Series C.
As Chief of Staff, Harry’s role evolved constantly. In the early days, he tackled whatever gaps existed: supporting customer success, building operational processes, helping recruit the first U.S. sales team. There were no playbooks, just problems to solve and opportunities to shape.
"Every six months, it felt like a brand-new job."
As Quantive scaled, so did Harry’s focus. He shifted from operational execution to coordinating leadership initiatives, leading offsites, and building the systems that would sustain growth. Along the way, he learned that the most valuable Chiefs of Staff aren’t just problem solvers - they’re force multipliers for leadership.
Trust, adaptability, and a bias toward action became his guiding principles.
"If you’re the opposite of your CEO in the ways that matter, that’s often a very good thing."
Making OKRs Work: Lessons from the Inside
At Quantive - a company that builds OKR software - Harry was naturally involved in OKRs, a topic that often falls into the realm of a Chief of Staff. Asked for best practices on OKRs, Harry shares that most OKR programs fail because they’re too rigid, too top-down, or simply disconnected from day-to-day work.
Harry’s approach was different. He focused on helping teams co-create goals that mattered — to the business and to them. That meant fewer objectives, more clarity, and creating space for real ownership.
“OKRs don’t work when they feel like homework. They work when people care about what they’re aiming for.”
Success came from building habits around reflection, focus, and learning - not just tracking metrics. The system Harry built prioritized alignment without killing autonomy.
For operators thinking about OKRs, his advice is simple: start small, stay human, and don’t confuse structure with bureaucracy.
What made OKRs work at Quantive:
Relentless focus: Limit OKRs to 1–2 key areas. Force tradeoffs.
Leadership buy-in: Founders and management need to be fully supportive of OKRs.
Designed for humans: Make sure teams want to participate — not just treat it like another checklist.
Built-in incentives: Celebrate wins tied to OKRs. Help teams see the personal upside in alignment.
Iterative improvement: OKRs weren’t static. Teams reviewed and refined them each quarter based on learnings.
"OKRs succeed when they are co-created, not dictated."
From Chief of Staff to Founder: OneTwo Growth
After five years at Quantive, Harry realized he’d scaled himself out of the day-to-day. The gaps he once filled were now covered, and he felt energized to help other companies navigate similar growth moments.
That led him to found OneTwo Growth, where Harry works as a fractional Chief of Staff and Strategy Advisor for startups.
He focuses on helping teams bring clarity and structure to strategy execution, without accumulating bureaucracy. His work often includes:
Coaching Chiefs of Staff to grow from operators into systems-thinkers
Helping leadership teams stay aligned as complexity increases
Designing effective frameworks that let strategy run on autopilot
"Startups don’t need more process - they need the right process that supports momentum."
OneTwo Growth is grounded in a systems-thinking approach: combining people, process, and technology to reach outcomes faster — and with less friction.
Advice for Aspiring Chiefs of Staff
Harry works with both current Chiefs and professionals keen to break into this role. He believes the best Chiefs bring a blend of curiosity, adaptability, and bias for action, not necessarily a perfect resume.
Here’s his advice for breaking in and thriving:
Your nontraditional background is an advantage: Organizations don’t want clones — they want complementary problem solvers.
Ask great questions in interviews: How does this company define "success" for the CoS role? Are they looking for a more administrative Chief or for an entirely embedded Chief running key projects?
Don’t try to be everything: Know your strengths. Lean into them, rather than trying to be perfect at every task.
Think like a builder, not a fixer: Focus on creating systems and capacity - not just solving today’s fire.
Invest in your network early: Build relationships with other Chiefs of Staff. Peer learning is invaluable.
"The worst thing you can do is say: 'I can do everything.' That doesn’t set you apart — it dilutes your value."
Harry’s journey shows that the CoS role is what you make of it. Done right, it’s not just a stepping stone but has the potential to be a career-defining experience.
Recommended Resources from Harry
As an active member and mentor in the Chief of Staff domain, Harry recommends the following resources to break into the role and level up:
Ask a Chief of Staff Slack community by Clara Ma - for connection and real-world advice.
The Art of Explanation by Ros Atkins - a book with fairly tactical advice to distill complex information for executive communication.
Your Chief of Staff — a newer community worth checking out, founded by Elise Kennedy.
These resources helped Harry sharpen his thinking and can help others at all stages of the CoS journey.
Thanks for Reading!
Hope you enjoyed this edition of The Operator. If Harry’s story sparked ideas or gave you a new lens on the Chief of Staff role, I’d love to hear from you — just hit reply or drop a comment.
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Until next time,
Jan
Super well done - Jan !