Founding Scaled Customer Success Manager

Outset invented a better way to do research: AI-powered user interviews.

Global brands like Hubspot, Microsoft, Uber and Nestle use Outset to achieve deeper, qualitative insights about their users at unprecedented speed and scale.

The research industry is massive (>$140B and growing) and ripe for disruption. Incumbents are outdated, slow, and burdened by high-cost services. That's our opportunity.

Outset is backed by top Silicon Valley investors and raised a $30M Series B in December 2025—less than six months after our Series A—led by Radical Ventures with participation from M12 (Microsoft’s venture arm), 8VC, Y Combinator, and Adverb Ventures.

The raise follows a breakout year, with our business growing 8x as enterprise customers across industries adopt our category, AI‑moderated research, as the new standard for understanding people.

We’re a tight-knit team serving some of the world’s largest enterprises.

As the Founding Scaled Customer Success Manager, you'll own adoption, retention, and growth across a mature portfolio of 100–200+ accounts in our Scaled segment — and you'll build the systems that make covering a book that size possible.

You'll determine the right signals, automate analysis and follow-ups, and design an operating model that gives customers an excellent experience. Roughly 70% of your time will be portfolio management; the other 30% will be building the infrastructure and process behind it — working closely with RevOps, Marketing, and Engineering.

This is a foundational hire. The health scoring, playbooks, and operating cadences you build will be the ones the team runs on for years, and you'll help define what "Scaled" means at Outset as the segment grows.

Responsibilities

• Own adoption, retention, and expansion outcomes across a portfolio of 100–200+ Scaled accounts, from onboarding through renewal
• Keep usage and adoption high in a deliberately lower-touch model — leverage programs, automation, and self-service before reaching for a calendar invite
• Monitor account health and usage signals to catch risk and expansion opportunities early, and prioritize where your direct time actually changes the outcome
• Run renewals across a mixed model of actively managed and auto-renewing accounts, partnering with our broader CS team on commercial approach
• Build and run one-to-many programs: onboarding cohorts, office hours, webinars, in-product guidance, documentation, and templated success plans
• Develop our account health tracking methodology from the ground up — what signals matter, how they're weighted, how they trigger action, and how we know the scoring is predictive
• Partner cross-functionally with RevOps, Marketing, and Engineering to build the infrastructure behind scaled CS: usage instrumentation, alerting, lifecycle triggers, and automated follow-up
• Design the operational cadence for this segment: what regular communication looks like, how issues route to and from Product Support, and what escalation looks like. (Product Support owns ticket resolution. You own the process around it).
• Build reporting in Hex and with other AI tools that gives the business real visibility into Scaled segment health, adoption, and retention
• Translate portfolio-wide patterns into prioritized input for Product

Qualifications

• 3–7 years in customer success, account management, CS operations, sales, or lifecycle/growth, including a high-volume portfolio
• Experience building scaled or digital CS programs from scratch, or working as one of the first hires in a scaled CS role
• Technically fluent and self-sufficient with data: product analytics and usage, pulling data with AI tools, and building tooling with AI
• Hands-on with a modern GTM and support stack. Ours is Pylon, Hex, HubSpot, Salesforce, and Claude; we lean heavily on AI day to day and expect you to as well
• Excellent written and verbal communication
• Series A/B/C or fast-paced SaaS experience, with a proactive, ownership-driven approach to ambiguity

Nice to have

• Experience defining or re-segmenting a customer base, or standing up a support model for a new segment
• Background in customer marketing, growth, or RevOps
• Familiarity with research operations or market research