[Hiring] VP of Operations, Software & Product @Plan Left

Role Description

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:

• Operations Side: Install and hold the operating cadence, build the systems that let the company scale, and keep the team accountable to outcomes.
• Product Side: Own product management across the portfolio, bringing a 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.

Qualifications

• A career that blends marketing and technology, understanding 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.
• Fluency with AI as a daily working tool, with strong prompting and custom Claude Projects or comparable workflows.
• 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 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.

Requirements

• Run the company on EOS, OKRs, or a hybrid that fits how the team works.
• Own the weekly cadence, the scorecard, and the accountability chart.
• Map and document the core processes for the business and each of its products.
• Own a single prioritized roadmap across the product portfolio.
• Bring a strong sense of UI and UX to every product decision.
• Stand up the marketing and go-to-market motions that produce new sales quickly.
• Build the operational backbone that supports growth.
• Grow a small team beneath you as the company expands.

Benefits

• Opportunity to start part-time and grow into a full-time seat across the year.
• Path to prove the model together and build the role around the value it creates.
• For the right candidate, willingness to go full-time right away.