About this role.
Chili Piper is seeking a senior product leader to own Orchestrator, a GTM control-layer product that detects signals across internal and external systems and initiates appropriate next actions. The Product Manager will define target audiences, validate customer and market problems, set product bets and success metrics, and drive adoption and business outcomes. This is a high-autonomy role that partners closely with Product Design and Engineering while retaining accountability for product direction, prioritization, and value realization. Ideal candidates bring senior B2B SaaS product management experience, comfort in technical and data-rich domains, and experience with integrations, CRM, or sales-engagement workflows.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would start with qualitative customer interviews, workflow observation, support and sales signals, and product-usage data to isolate a segment with an urgent, repeatable problem. I would document its trigger, desired outcome, current workaround, and measurable value, then test the smallest coherent solution with that audience before expanding scope.
I would evaluate each request against the target audience, problem severity, expected adoption, business impact, strategic fit, technical viability, and maintenance cost. I would favor a small set of composable capabilities that keeps the decisioning system predictable rather than accepting one-off edge cases that dilute the product.
I would track activation and first-value time, eligible-workflow coverage, configuration completion, automation execution reliability, user trust signals such as overrides or disablement, and repeat usage. I would connect these to customer outcomes such as meeting recovery, lead conversion, response time, and retention or expansion where attribution is credible.
I clearly define the customer problem, intended outcome, constraints, success measures, and priority rationale, then involve engineering early to explore viable options and tradeoffs. I respect engineering ownership of the technical solution while ensuring the selected approach remains aligned with customer value, adoption needs, and a coherent product experience.
I use AI to accelerate research synthesis, draft hypotheses, analyze structured feedback, and prototype workflows, while validating outputs against source evidence and user research. For customer-facing AI features, I define the failure modes, transparency requirements, controls, and evaluation metrics before treating the capability as production-ready.
About Chili Piper
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’re looking for a Senior Product Manager to lead Orchestrator, Chili Piper’s GTM Control Layer.
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.
Orchestrator listens for signals across Chili Piper and external tools, decides what should happen next, and takes the action itself. That includes catching a form abandonment, a no-show, a missed meeting, or a cold chat, checking ICP fit, account ownership, intent history, and CRM state, then firing the right next step: enrolling a sequence in Salesloft, Outreach, or Gong Engage, notifying a rep, rescheduling a meeting, or sending a booking link.
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.
What you’ll do
Own Orchestrator 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 signal detection, decisioning, and action-taking 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 signal types, decision logic, and external integrations coherent, so the system stays predictable and trustworthy as it grows
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
What we’re looking for
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
Nice to have
Experience building or owning third-party integrations, especially with CRM, Sales Engagement, 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
Who this role is for
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.
How this role works
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
Additional Information
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.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
Upload your resume now
- To unlock remote work opportunities and be discovered by global employers.
This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content.
