THE OPPORTUNITY
Gesture's engineering team is shipping fast across our mobile app and B2B platform, and we need someone who can turn ambiguity into a clear, prioritized roadmap — translating what the business and customers need into what engineering actually builds next.
This role sits between the CEO/leadership and the engineering team. You are the person who makes sure the right things get built, in the right order, for the right reasons. You are not a note-taker in standups. You own the "what" and the "why" so engineering can own the "how."
We're open to structuring this as a fractional Head of Product engagement to start, with a path to full-time as scope and trust grow.
WHAT YOU WILL OWN
- The product roadmap for our mobile app and/or B2B platform, prioritized against business and revenue goals
- Translating CEO and leadership vision into clear specs, user stories, and acceptance criteria engineering can execute against
- The backlog: grooming, prioritizing, and making the hard calls about what doesn't get built this sprint
- Sprint planning and delivery cadence in partnership with engineering leads
- Bridging engineering with Sales, B2B, and Consumer teams so product decisions reflect real customer and market needs
- QA of shipped features against the original intent, closing the loop between what was asked for and what was delivered
- AI/data product surface: matching logic, data enrichment strategy, and analytics offerings
WHAT THIS ROLE IS NOT
Let's be clear:
- This is not a project coordinator role that just schedules meetings and updates a Jira board
- This is not a role for someone who needs a fully-staffed PM org to be effective
- This is not a "build slides about the roadmap" job — you own the roadmap
- This is not a role for people uncomfortable saying no to stakeholders, including leadership
WHAT YOU WILL BE HELD ACCOUNTABLE FOR
I. Product Strategy & Roadmap
- Build and maintain a prioritized roadmap for engineering, grounded in business impact
- Partner with the CEO and engineering leads to translate high-level vision into concrete, sequenced initiatives
- Continuously reassess priorities as the business and market shift
II. Execution & Delivery
- Write clear specs, user stories, and acceptance criteria
- Run or support sprint planning, backlog grooming, and release cadence
- Track delivery against plan and flag risk early, not after it's a fire
III. Cross-Functional Translation
- Act as the connective tissue between engineering and Sales, B2B, and Consumer Mobile App teams
- Gather and synthesize feedback from customer-facing teams into actionable product requirements
- Represent the "why" behind engineering priorities to the rest of the company
IV. Quality & Feedback Loop
- Validate shipped work against original intent before it's called "done"
- Build a lightweight process for gathering user/customer feedback post-launch
- Identify recurring gaps between what was requested and what was built, and fix the process causing them
WHAT SUCCESS LOOKS LIKE
In 30 days: You understand the current roadmap, the engineering team's workflow, and where the biggest gaps in clarity or prioritization exist.
In 60 days: There's a clean, prioritized roadmap the whole company can see and trust. Sprint planning has real structure.
In 90 days: Engineering is shipping predictably against a roadmap tied to business outcomes, with fewer surprises and less rework.
WHAT YOU MUST HAVE
- Experience as a Product Manager (or equivalent) in a fast-moving tech or startup environment
- Comfort writing clear specs and user stories that engineers can actually build from
- Experience running or contributing meaningfully to sprint planning and backlog prioritization
- Ability to work directly with engineering, sales, and leadership in the same week
- Strong written and verbal communication — you can explain the "why" as clearly as the "what"
- Comfortable with ambiguity and shifting priorities in an early-stage environment
- Available to work onsite in NYC/Denver on a hybrid basis
BONUS KNOWLEDGE
- Experience with mobile app and/or B2B SaaS platforms
- Background working directly with or alongside engineering teams (technical enough to earn credibility, not necessarily a former engineer)
- Experience in a marketplace, AI/ML, or logistics-driven product
- Prior experience scaling a part-time or fractional role into full-time as the business grew
HOW YOU OPERATE
- Structural Clarity: You break ambiguity into a clear roadmap, not the other way around
- Bias for Action: You make prioritization calls with incomplete information and adjust as you learn
- Ownership: You close the loop — you don't consider something done until it matches intent
- Ego-Free: Your success is measured by what engineering ships and how well it serves the business, not your own visibility
WHO SHOULD NOT APPLY
- You prefer building decks about the roadmap to owning the roadmap
- You need a fully-staffed PM org or perfect conditions to be effective
- You avoid making the hard call about what doesn't get built this sprint
- You're uncomfortable saying no to stakeholders, including leadership
- You consider a feature "done" when it ships, not when it matches original intent
COMPENSATION
- Full-Time Range: $100,000 – $120,600 / yr
- Final compensation determined by scope (part-time vs. full-time), experience, and fit
OTHER GESTURE BENEFITS AND PERKS
- Full benefits: health, dental, vision, equity and stock options (full-time)
- Make a Gesture Day: Each employee receives the chance to earn credit to send a surprise gift to someone they admire — living the company mission firsthand
- Gesture Swag Pack: exclusive branded gear (hoodie, water bottle, or cap)
- Beautiful HQ Experience: Modern New York office with creative work zones, media studio, and collaboration spaces
- Paid Team Lunches or Coffee Hours: Casual networking with leadership and cross-department peers