VP of Operations, Software & Product at Plan Left

About The Role

This is the seat that turns vision into a running business. You will work directly with the founder as the operational counterpart to his direction, owning the day to day across the product business so it runs on systems rather than on his attention.

The role spans two worlds. On the operations side, you install and hold the operating cadence, build the systems that let the company scale, and keep the team accountable to outcomes. On the product side, you own product management across the portfolio. You bring the rare combination of a marketing and technology background, an eye for good product, and the operational discipline to make a small company run like a much larger one.

What You'll Own

• The Operating System. You run the company on EOS, OKRs, or a hybrid that fits how the team works. You own the weekly cadence, the scorecard, and the accountability chart, and you hold people to their commitments.
• Operational Excellence. You map and document the core processes for the business and each of its products, then improve them so output per dollar and per hour keeps climbing as the company grows.
• Product Management. You own a single prioritized roadmap across the product portfolio, translate strategy into shipped work, and keep status visible so nothing stalls in the gap between idea and release.
• Product Quality. You bring a strong sense of UI and UX to every product decision and hold the bar on what good looks like, whether you are shaping it yourself or directing the people who do.
• Growth. You stand up the marketing and go-to-market motions that produce new sales quickly, giving the business the momentum that funds its next stage of growth.
• Scale. You build the operational backbone that supports growth, and you grow a small team beneath you as the company expands.

Your First Six Months

These are the early wins that prove the model is working and that earn the full time seat.

• Install the Operating System. Stand up EOS or OKRs with a weekly cadence and a live scorecard, so the team runs on a rhythm everyone can see.
• Document the Core Processes. Capture the core processes for each product and get the team following them, so the business runs on systems rather than memory.
• Own the Product Roadmap. Bring the portfolio onto one prioritized roadmap with status visible, so everyone knows what is shipping and when.
• Produce Early Revenue. Build the go-to-market motions that bring in new sales, giving the role momentum and funding its growth.

The Background We're Looking For

• A career that blends marketing and technology, so you understand both how products get built and how they get sold.
• A strong eye for UI and UX, ideally with a design background or hands-on design experience.
• Comfort working alongside technology and product teams, without needing to be deeply technical yourself. Terminal level skills and a developer background are a bonus, not a requirement.
• Fluency with AI as a daily working tool, with strong prompting and custom Claude Projects or comparable workflows you have built to get real work done.
• Hands-on experience running EOS, OKRs, or a similar operating system inside a real company.
• A track record of operational excellence, with examples of processes you built that made a team faster, cleaner, and more accountable.
• Product management experience across more than one product, with the judgment to prioritize across competing roadmaps.
• The range and judgment of a senior operations leader who can own the entire operation, from systems and team to product and growth.
• A strong bonus if you have already built, scaled, and exited a software company, because you will recognize this path from the inside and know where it tends to bend.

How We Work Together: Kolbe Fit

We use the Kolbe A Index to build teams that fit together well. Kolbe measures how a person instinctively takes action when they are free to work their own way, which is a different thing from intelligence or personality. It scores four modes: Fact Finder, Follow Thru, Quick Start, and Implementor. We lean on it because the right match of working styles is what lets a small team move quickly with very little friction.

You will work side by side with the founder, whose Kolbe A Index is 7-3-3-6. He leads with Fact Finder, which means he sets direction through research and gathers information before he commits. He accommodates in Implementor, so he engages with tangible builds and physical work when the project calls for it. His Follow Thru of 3 keeps his options open and his structure loose, which means he starts more than he finishes. This seat is the complement to that.

The ideal profile for this role is around a 7-7-5-5. You match his depth in Fact Finder, so the two of you share the same instinct for research and evidence and communicate easily about how decisions get made. You pair that depth with the long Follow Thru that turns ideas into systems, sequences, and finished work. That Follow Thru is the heart of this hire, because it brings order and completion to the founder's natural drive to keep generating new directions.

Two numbers carry the most weight in this seat. A Fact Finder of 7 or higher signals that you operate from the same research-driven foundation he does. A Follow Thru of 5 or higher signals that you bring the structure and completion this role exists to provide. We weigh both heavily alongside the rest of our evaluation, because together they describe the working partnership this seat is built around.

The Details

Ideally you come in part time and grow into the full time seat across the year, with the hours expanding as the operation takes hold and the scope grows. That path lets the two of you prove the model together and build the role around the value it creates. For the right candidate, we are willing to go full time right away, which is the natural fit for someone leaving another role who wants to commit fully from day one.

Either way, the destination is the same. You come in to install the operating system and prove the model at a high altitude, and the role builds toward a full time leadership seat. You report directly to the founder, and you own the result.