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Chili Piper is a B2B SaaS company that helps GTM teams turn inbound leads into qualified meetings - instantly. Our Demand Conversion Platform makes it easier for buyers and sellers to connect fast, without the usual friction in the funnel.
We’re a fully remote, global team that loves building solutions that truly help our customers, moving fast, and having fun while creating something meaningful. We’re growing quickly and aiming big!
We are looking for a Product Manager to lead ChiliCal, Ecosystem, and Handoff, three connected product areas at the heart of the customer experience.
Internally, we think of this role as a Product Market Fitter. This is not a traditional roadmap management role. It is a product leadership role for someone who loves building complex, enterprise-grade products and has the judgment to turn customer and market evidence into focused product bets that drive real adoption and business impact.
This area includes the surfaces customers interact with every day:
ChiliCal is our scheduling and calendar engine: meeting types, availability, scheduling links, the Booking App, reschedules, reminders, and the Fire extension inside Google Calendar.
Ecosystem is the set of integrations that connects Chili Piper to the rest of the revenue stack, including Salesforce, Google Calendar, Microsoft Outlook, Microsoft Teams, Zoom, and Gong.
Handoff is routing and distribution: the Handoff Router, round-robin, queues, and the logic that ensures a lead gets owned by the right rep.
You will own the full arc of a product bet: target customer, first audience, market and customer evidence, problem definition, intended outcome, value, viability, priority, success metrics, first adoption trigger, usage learning, and business outcome.
You will own the solution concept, meaning what we offer and how it is offered. You will not own solution architecture, implementation, or product enablement execution. You will partner closely with a Product Designer and a Product Engineering Lead to shape solutions that are valuable, coherent, and practical to deliver.
This role requires strong judgment, comfort with ambiguity, and the ability to turn complex workflows, data, and customer needs into clear product direction. It is a strong fit for someone who wants to build products that solve real problems for sophisticated users and who measures success by whether customers actually adopt what gets built.
Own ChiliCal, Ecosystem, and Handoff end to end, from market and customer evidence through adoption, iteration, and long-term business impact
Define the first audience for every bet and protect that focus as new requests, edge cases, and opportunities emerge
Identify the right problems to solve and turn complex scheduling, integration, and routing workflows into clear product direction
Define value, viability, priority, and success metrics, including what should trigger first adoption
Monitor adoption and real usage after launch, then use what you learn to improve the product and shape what comes next
Keep these connected surfaces coherent, so changes across ChiliCal, Ecosystem, and Handoff work together rather than against each other
Partner with Product Design on the experience, first-use path, and product-side enablement
Partner with the Product Engineering Lead on solutions that are technically sound and practical to deliver
Prioritize ruthlessly and make clear calls when the problem is complex and the answer is not obvious
Hold a high standard for quality. You do not ship things you would not want to use yourself
Senior-level experience managing complex B2B SaaS products, with clear ownership of a product area or major initiatives
Strong product judgment, with the ability to find problems worth solving and make informed tradeoffs in ambiguous environments
Hands-on use of AI tools in day-to-day product work, with good judgment about where AI genuinely improves a product experience
The ability to simplify complexity and turn customer evidence, data, and technical constraints into clear product decisions
Deep curiosity about users and markets, and a habit of building conviction through direct evidence
Comfort in technical domains and credibility with technical users and engineering partners
A bias toward focus and shipping narrow to learn quickly
Experience working closely with Engineering, Design, and cross-functional partners in a fast-moving environment
The drive to build products that solve real problems and get used, not just shipped
Experience with calendar, scheduling, or meeting workflow products
Experience building or owning third-party integrations, especially with CRM, calendar, or conferencing platforms
Experience with lead routing, distribution, or assignment logic
Experience with CRM or marketing automation platforms
Experience building enterprise-grade, data-rich SaaS products
Experience building or shipping with Claude or similar products
This role is best suited to someone energized by high ownership, independent judgment, and making decisions without a playbook. We give people real responsibility and a lot of room to operate, which means you will be expected to run your area, set direction, and make hard calls with imperfect information.
If you are looking for a highly directed environment with a lot of structure around what to do next, this is probably not the right fit.
We care deeply about clear ownership and close cross-functional partnership.
The Product Market Fitter owns the target customer, problem, intended outcome, value, viability, priority, adoption, and business result
The Product Designer owns the experience and product-side enablement
The Product Designer and Product Engineering Lead jointly own solution architecture
The Product Engineering Lead owns the technical solution and delivery execution
Why you'll love being a part of our team:
Our team loves Chili Piper because we’re building the company of the future.
Work with an immensely talented global team
Work in a business that’s run fairly and transparently
Competitive pay based on market rate wherever you live
We lead by example--showing industry peers and leaders how to innovate, improve, and grow--while having fun
How we work:
Freedom and flexibility. We’re a 100% distributed team working from around the world, and we've been fully remote since 2016. Our team members can work from wherever they want in the world, as long as they show up on our weekly all hands meeting on Zoom.
Solve interesting problems. The software landscape has exploded. There are dozens of solutions for each problem. We want to be different. We come up with new angles on existing problems or invent better solutions to help companies with their sales and marketing. Then we turn these ideas into beautiful, smart software.
Autonomy and ownership. Working on a distributed team means you don’t have someone micromanaging you or looking over your shoulder to make sure you’re getting things done. We’re a team of do-ers who take full ownership for their results.
Be helpful. Our first value as a company is help. Help our customers be successful. Help our prospects get the right information and make the right decision whether or not it includes our products. Help our team members reach their full potential.
The perks:
Unlimited vacation (and we do mean it, and we do take it!)
Generous health, dental, and vision insurance
Any equipment/software/tech that you need to do your job
Annual professional development stipend of $2,000 USD
Equity - all Pipers receive stock options
Annual company retreat in epic locations (past trips: Paris, Morocco, Tulum, Iceland, Ibiza, India). Check out the video from last year’s retreat in Tenerife.