Senior Product Manager

About Sidepocket Financial

95\.8% of self-employed Americans claim zero retirement deduction. Not because they do not want to save. Because no one built the automation for them. That is 23 million Schedule C filers leaving $659 billion in retirement deductions unclaimed every single year.

Sidepocket Inc., doing business as Sidepocket Financial, is the company built to close that gap. We are a SEC-registered RIA (CRD# 312031) with a patented (patents pending) platform that automates retirement savings and investing for the self-employed. The Tactical IRA platform selects the right account, calculates safe contributions from variable income, and invests with fiduciary oversight. One platform, zero decisions required for the client.

The Opportunity

This is a Senior IC role and a hands-on one. No direct reports on day one. You own the roadmap, you design the features, you write the specs, you sit with engineering, you ship. You are the first dedicated product hire at a company where the product function will be defined by how you operate.

Product Owner, Not Product Manager

This role is not a ticket-writing job. You own the product. That means you design features, write copy, build flows, make trade-off calls, and decide what ships next. Every future feature of Tactical IRA will be decided by you alongside the GTM Engineer and the COO, with the market plan as a core input.

If you are the kind of PM who hands a half-baked spec to a designer and waits, this is not for you. If you open the design tool yourself, sketch the flow, test it on your phone, rewrite the copy three times, then hand engineering something they can build without a meeting, keep reading.

Why This Role Exists

The foundations are set. V1 is live. Hundreds of hours of customer development with prospective clients and CPA partners have already mapped what works, what does not, and what comes next. What is missing is the full-time product owner who turns that foundation into a refined, growing product through daily sequencing decisions, hands-on design iteration, and tight coordination with GTM. You are the PM who takes v1 to v10, with clear KPIs to hit inside 12 months.

The Role

You take over the product roadmap from the founders on day one. You inherit a live v1, a synthesized library of customer development research, and a clear picture of what is working and what needs to change. Your job is refinement and sequencing: deciding what ships next, in what order, and why, so the product keeps pace with what GTM sells and every release moves a KPI.

The right person designs fluently, writes copy that does not sound like a bank, and understands retirement accounts well enough to have opinions about edge cases. You treat compliance as a design constraint, not an obstacle. You write dense, direct specs. No filler, no hedging, no AI-sounding language.

Core Responsibilities

• Product Roadmap, Design, and Specs:

You own the roadmap and the pixels. You decide what ships next, in what order, and why. You design the screens, write the copy, write the specs, and sit with engineering on implementation and trade-offs.

• Hands-On Product Design:

There is no separate designer. You are it. You own typography, layout, flows, states, error handling, empty states, and microcopy. You make the product feel like something self-employed earners trust with their retirement.

• Every Feature Decided Alongside the Marketing Plan:

Product and GTM are one conversation at this company. You work directly with the GTM Engineer and COO to decide what ships next based on what the market needs, not what is interesting to build. Every feature has a distribution story before it has a spec. Every spec has a distribution plan before it ships.

• Client-Driven Iteration:

You talk to clients. You watch the sessions. You read the support tickets. You run validation sessions with prospective clients and CPA partners. You are the person who knows, with evidence, whether the product does what clients actually want, and you fix the places where it does not.

• CPA Channel Product Surface:

Our primary distribution channel is CPA partnerships. You design and build the surface that makes signed CPAs active and active CPAs productive, and you ship the instrumentation to prove it.

• Onboarding and Dashboard:

These are the two surfaces where clients decide whether to trust us and whether to stay. V1 is live. You own what comes next. You watch sessions, read the feedback, run the tests, iterate weekly.

• Pricing, Packaging, Retention:

You own the math behind why a client stays and the product work that makes staying obvious. You ship the instrumentation, you read the cohorts, you propose the changes.

• Compliance-Aware Product Work:

We are an SEC-registered RIA. The CCO has authority over compliance-impacting copy and flows. You work with him as a design partner, not a gatekeeper. You know which product decisions need a compliance review and which do not.

• Weekly Product Reporting:

You set targets with the COO, build the instrumentation, and deliver a written product report every Friday. What shipped, what the numbers say, what you are changing next week, and why.

Tools and Stack

You will be expected to work fluently with modern product design and instrumentation tools, and to extend the stack where it makes sense.

Expected Proficiency

• Design fluency:

Figma, Framer, or equivalent. You design, you do not just review.

• Code literacy:

You can read modern frontend code and reason about trade-offs with engineers. You do not need to ship production code, but bonus if you can make copy, layout, and flow tweaks yourself.

• LLM-assisted product work:

Claude, ChatGPT, or equivalent for spec drafting, copy iteration, and rapid prototype reviews. You use these tools daily.

• Product instrumentation and analytics:

You can design what to measure, instrument it, and read the output.

• Spec writing:

Clear acceptance criteria, edge cases called out, state transitions explicit. Engineers should not need to ask you what you meant.

• Regulated-product comfort:

You know what an RIA is and why a CCO exists. You have worked inside compliance regimes before, or you will learn fast because you respect them.

Ideal Candidate Profile

Required

• 5\+ years shipping consumer or prosumer fintech as a PM who also designs. You owned roadmaps and you owned pixels.
• You have owned a product at a company under 30 people and shipped without waiting for process, designers, or permission.
• You can open a design tool and design a flow yourself. Not review, design.
• You write dense, direct specs and copy. No filler, no hedging, no AI-sounding language.
• You have worked inside regulated products or you are genuinely comfortable working inside compliance constraints.
• Track record of hitting measurable product KPIs (conversion, retention, activation, revenue per user) at an early-stage company.
• You understand equity-driven compensation and you are motivated by it. You have taken this kind of bet before, or you are ready to now for the right team.

Strongly Preferred

• Experience in retirement, tax, or small-business finance products.
• Experience building for self-employed, freelancer, or 1099 workers.
• Prior work as the first or founding PM at a company under 15 people.
• Familiarity with SEC/FINRA advertising rules or comparable compliance regimes.
• Experience working directly with CPAs, tax preparers, or accountants as a user segment.
• Portfolio of actual shipped UI (not just wireframes, not just mocks that never shipped).

Why This Role, Why Now

You are not joining a startup chasing an unproven idea. You are not joining a startup starting from zero either. You are joining a startup that has done the hard work most founders skip: hundreds of hours of customer development, signed partnerships, SEC registration, patents filed, a technical foundation in production, and a live v1 ready to be refined into something that scales. What is missing is the person who owns the product function full-time and turns that foundation into a compounding product, in lockstep with a GTM function ready to turn output into growth.

• The Team:

You work alongside people who built security infrastructure at PayPal and Chime, managed half the server loads at Dropbox, founded industry-creating companies, and quants and cryptographers with 25\+ years of experience. Most are mostly-equity because they got to where they are today from startups and equity. They know what they are doing and why they are here.

• Category Creation:

No competitor solves all the barriers in this market. The large incumbents cannot serve the self-employed profitably. The well-known robo-advisors solve a fraction of the problem. You are not competing for PM scope. You are defining the product function at the company that creates the category.

• V1 Live, Foundations Set:

Hundreds of hours of customer development with prospective clients and CPA partners. Signed CPA partnerships. Early clients. Modest revenue. V1 in production. The foundation is laid. You are the PM who refines it into something that compounds.

• Ground-Floor Equity:

Mid-fundraise. Equity-heavy, modest cash. Your equity reflects foundational timing at a company with defensible IP, regulatory moats, and a market that is 95\.8% untouched. This is the kind of equity stake that changes trajectories when the company works.

• Refine and Sequence, Not Build From Zero:

You are not inheriting a blank page. You are not inheriting a polished product either. You inherit a live v1, a synthesized research library, a technical foundation, and a team. Your job is to decide what ships next, design it, and ship it.

• Direct COO and CEO Access:

You report to the COO and work directly with the CEO on roadmap, product strategy, and iteration. No layers. No bureaucracy. You are the first dedicated product hire.

• Integral Team Member:

You become part of the San Francisco core team alongside the founders, CCO, and engineering leads. If remote, you visit SF at least once per month to stay embedded in strategy, product direction, and team rhythm.