VP of Product | REMOTE

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Work from anywhereSenior$250K–400K/yrPublished 12 October 2026Looks fresh

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First recorded by Psst: 9 November 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.

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The 20-second read

Experience
Senior
Where you can live
Work from anywhere
Skills and tools
slack, shopify, b2b, saas, knowledge base
Job type
Full-time

Read from the ad by Psst's rules. Check the full ad below before applying.

Job details

Where you can work
Work from anywhere
Employment type
Full-time
Advertised pay
$250K–400K/yr
Experience
Senior
Employer publication date
12 October 2026
First recorded by Psst
9 November 2026
Last checked at the source
10 November 2026

About the job

About the company

The company is the #1 ERP in the cannabis industry with $15B in sales processed through our platform. We've built a battle-tested ERP and B2B eCommerce platform that powers inventory, manufacturing, sales, and logistics, and we're now building AI infrastructure on top of it to give commercial businesses their all-in-one AI stack.

We're growing and profitable, with 5/5 stars on Glassdoor. Our investors include Felicis Ventures, Global Founders Capital, Poseidon Asset Management, and Village Global, who have funded companies such as Shopify, Cruise, HelloFresh, Facebook, Slack, and Opendoor.

Get to know the team, our culture and our full benefits at the company

The Role

AI has hit an inflection point in model capability for enterprise work, and AI assistants like Claude, Codex, and Grok are seeing record adoption in the workplace. We believe the system of record has never been more valuable, because it's where the data AI acts on gets consolidated and organized.

So we're building the company headless-first: unified access to ERP data, deep MCP and embedded AI assistant integrations, agents embedded in the company, and a seamless experience between the ERP and the AI tools our customers already use.

The AI space moves fast and the specifics will change, so this vision is something you'll mold.

As our first VP of Product, you'll own

Product direction: strategy across the company ERP, the company Commerce, Order Agent, the company Analytics, and our AI product suite, with accountability to revenue & growth

AI product suite: the foundations that make the company an all-in-one AI stack, including the unified data layer, agent builder, workflow builder, MCP, and the headless experience

AI vision and evangelism: keeping the company ahead of the curve on AI, finding where it creates product-market fit and new market opportunities, and championing that vision with the team, customers, and the market

Product org: growing the product team from 4 to 8+, structured to serve existing ERP and Commerce customers while building new AI-first product lines

Product timeline: the company's source of truth for what's shipping and when

AI-first product process: how the team plans, specs, designs, and ships with AI

And more…

You'll report to the CEO and work closely with the VP of Engineering, Head of Sales, Head of Go-to-Market, and the product team. You'll have a long-tenured team of craftspeople around the existing product, and a fast-moving AI team experimenting at the frontier. There's a lot of autonomy and room to bring new methods, and we welcome wild AI-forward ideas.

What you'll do

Product strategy

  • Deliver a quarterly strategy review to the exec team: market landscape, ERP and AI sequencing, a 1-year roadmap, metrics, and resourcing asks
  • Own the product timeline and keep the company and technical teams aligned on it
  • Shape our data infrastructure (StarRocks, BigQuery, Postgres) with engineering so it serves internal and external AI use cases

AI vision and evangelism

  • Track new models, AI tools, and competitor moves, and turn them into a point of view on where the company should play next
  • Find product-market fit for our AI products and size the new markets AI opens up, testing bets with customers before we commit the roadmap
  • Evangelize our AI vision inside and outside the company: rally the team, equip GTM with the story, and show customers and the industry what an AI-first ERP can do

Team leadership

  • Own the product hiring pipeline, set the hiring bar, and find creative ways to bring in top talent
  • Manage and coach the product team, including hard feedback, performance plans, and exits when needed
  • Set PRD standards, review PRDs, designs, and mockups, and lead the team's adoption of AI-first product processes

Cross-functional leadership

  • Set the operating cadence with engineering: planning, roadmap reviews, and a clear split where product owns the what and engineering owns the how
  • Work with GTM on launches, feature enablement, and AI-forward content, and make sure our MCP and API docs and knowledge base are high quality
  • Run the feedback loop from customers, CS, and Sales, build relationships with key customers, and track feature adoption in a way the whole company can see

What success looks like at 6 months

  • You've run your first quarterly strategy review, and the exec team has signed off on a 1-year roadmap tied to revenue targets
  • You've made your first product hires, at a hiring bar you've set and written down
  • You've shipped a core piece of the headless AI suite, and its adoption and revenue impact are tracked in a dashboard the whole company uses

What we look for

AI fluency

For every AI role, we look for three things

  • Tool fluency: you personally build with AI tools. You go beyond prompting and have built your own skills, agents, workflows, or prototypes.
  • Process fluency: you've set AI-first processes for a product team, and you have a point of view on how to evaluate AI fluency when hiring a PM.
  • Build fluency: you know how to evaluate an AI workflow in production, with evals, observability, and feedback loops that make agents better over time.

You use AI tools daily and can tell us specifically where your fluency is strong and where you're still building it.

Must have

  • 10+ years in product management, including 4+ leading product teams
  • Product leadership: you've built and run a product org, including hiring, coaching, and making hard people calls, and you've led a product into new markets or major new product directions
  • AI products in production: you've built and shipped AI product lines such as MCPs, Agent Builders, Workflows, Copilots, etc… that are used in production
  • Technical depth: you know the modern SaaS and AI stack, including infrastructure, data, AI models, and full-stack development, and the production concerns that come with it: reliability, observability, permissions, and durable workflow execution
  • Outcome orientation: you measure the impact of product decisions by their revenue impact
  • Hands-on: you still do the work: PRDs, tools, details. You can sit with engineers without translating through a layer

Strong signal

  • Experience in ERP, accounting, cannabis, or supply chain software
  • You've taken an AI product from zero to revenue
  • You've led product at a B2B SaaS company at a similar stage
  • You've been a founder

How we work

  • We love building with AI. Trying new models the week they drop, building agents for fun, and forming strong opinions on what works. We invest in it with company-wide AI growth with classes and workshops, AI demo days, AI hackathons, and access to best-in-class models and tools.
  • Product owns outcomes, not output. You measure product by adoption and revenue, and you hold the team to the same bar.
  • Taste and conviction beat consensus. You make opinionated calls on what we build, and you grow that taste across the product team.
  • Product owns the what, engineering owns the how. You hold a high technical bar without doing engineering's job.
  • You'll build on what we've learned. You'll have access to the team's combined AI knowledge and the processes and skills we've built.

For the full picture of our culture and who thrives here, see the company .

Benefits

Our careers page is the best way to get to know us: the full benefits, our yearly offsites, who thrives here, and what the team says about working at the company.

Here are a few highlights (exact benefits vary by country and employment type):

Fully remote across 4 continents

Employee-friendly option terms: after 2 years, a 10-year window to exercise if you leave

18 days PTO + 11 holidays (sick days don't count toward PTO)

Medical, dental, vision + 401(k) for US employees

The best AI tools available and a generous AI stipend for everything else

Yearly in-person team offsites

Interview process

Application questions: three short questions on something you've built with AI, an AI capability you've shipped, and the product teams you've led

Leadership interview (60 min): your background, how you lead, hire, and manage product teams, and a briefing on the role

AI product-market fit (60 min): your view of AI product-market fit for the company, plus a show and tell of products and mockups you've built

Co-building session (90 min): build a working prototype of a feature live with AI, alongside our design and product team

Technical leadership (60 min): how you work with engineering, what makes an MCP and headless suite defensible, and how product improves agents over time

Take-home: Headless AI Product Suite (4–8 hours, then a 60 min presentation): define the company's headless AI product suite and present it live

Meet the team (four 45 min calls): calls with both co-founders, a reverse AMA with GTM, and an AMA with the product team

References and offer

The company was formed by an environment of mutual respect and trust made up by people working together without regard to race, color, religion, sex, pregnancy (including childbirth, lactation and related medical conditions), national origin, age, physical and mental disability, marital status, sexual orientation, gender identity, gender expression, genetic information (including characteristics and testing), military and veteran status, and any other characteristic protected by law. We believe that diversity and inclusion among our team members is critical to our success and we proactively strive to recruit, develop and retain the best and brightest people from the most diverse candidate pools we can find all over the world.

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