Vice President of Customer Success

About the role

Time Doctor is hiring a VP of Customer Success to own retention across a global base of 10k+ customers spanning a hybrid product-led and sales-led business. The foundation is built: a rebuilt Customer Success Playbook, three teams in place, and a clear operating model. Your mandate is to make it perform — and to build customer success as an AI-first function from the ground up. You'll report to the CEO, partner closely with the CRO and revenue team, and lead Account Management, Support, and Solutions as one integrated post-sale organization.

Who we are

Time Doctor is a workforce analytics platform that provides distributed teams the visibility they need to improve trust and performance. We serve remote, hybrid, and outsourced/shared services organizations worldwide, especially in BPO, healthcare, and tech services. We're bootstrapped, profitable, and fully remote, with about 125 people across 30+ countries. We've built a durable business on customer revenue, not venture capital. Now we're scaling it.

The role

You'll lead everything that happens after the sale — Account Management, Support, and Solutions (including onboarding) — as one integrated function with one job: keep and grow every dollar of customer revenue.

Three things make this seat different from most VP of Customer Success roles:

• The number. You own Net Revenue Retention outright — protecting revenue through renewals and saves, and growing it through an owned expansion number driven in partnership with our CRO and revenue team. Retention is our #1 company priority, and this role is where it lives.
• The playbook. We've already rebuilt the CS Playbook from the ground up: account segmentation and tiering, AM pod structure, health scoring, engagement plans (save, revenue, and success plans), EBRs, and a defined operating cadence with renewal and expansion processes. This is not a build-the-process-from-scratch role — it's a lead-and-execute role. Your job is disciplined, consistent execution across a global remote team, and sharpening the system with data as we scale.
• The operating model. You'll operate as a player/coach in an AI-first organization — building and orchestrating agents yourself, embedding them in daily operations, working side by side with Account Managers, and scaling a lean team that does the same.

Who you are

• You wake up thinking about retention — every renewal, every save, every expansion opportunity in the base.
• You hold yourself to a simple standard: no surprise churn. Risk gets caught early and worked hard. Always.
• You see sales leaders as partners, not rivals for credit — a shared revenue goal with the CRO is what excites you.
• You're happiest in the work: side by side with an AM on a save plan, or in front of a customer's executive team.
• You run systems with discipline. A playbook is only as good as its execution, and execution is your craft.
• Today's AI landscape energizes you, it doesn't scare you. You "nerd out" on agents and automation — and you build first, delegate second.
• Entrepreneurial and scrappy: you deliver results without waiting for the perfect budget or team size.
• You're competitive, hungry, and coachable — you've been coached, you seek out coaches, and you look for every edge you can get.

What you'll own

• The number. Net Revenue Retention across the installed base — Gross Revenue Retention and churn as the floor, plus an owned expansion number: identifying, qualifying, and driving upsell, cross-sell, and seat growth in partnership with the CRO and revenue team, with shared pipeline visibility and clean handoffs.
• Playbook execution. Disciplined, consistent execution of the CS Playbook across every pod and region — segmentation, engagement statuses and plans, health scoring, EBRs, and the weekly/monthly/quarterly cadence — refined with data, not rebuilt on instinct.
• Key accounts. Executive sponsorship of our most strategic customers. You personally own senior stakeholder relationships, step into high-risk renewals and escalations, and drive them to fast decisions.
• Onboarding and time-to-value. Implementation and early lifecycle outcomes through the Solutions team, so customers see value fast and stay.
• The support experience. Service quality, responsiveness, and effectiveness across regions and segments.
• The AI-first operating model. Agents and automation embedded in daily CS operations — risk detection, customer coverage, EBR prep, support responsiveness, reporting — so a lean team outproduces a big one.
• The team. Hire, develop, and lead team leads and ICs across Account Management, Support, and Solutions in multiple time zones — and grow their AI fluency so they build and scale their own agentic workflows.

This role is NOT for you if…

• You manage retention from a dashboard and don't like a calendar full of customer calls. This is a hands-on role — side by side with AMs, in the accounts, in the escalations.
• "AI experience" on your resume means your team uses ChatGPT sometimes. We need someone who has personally built and orchestrated agent workflows that ship real work and deliver real outcomes.
• You need to design your own process to succeed. The playbook is built. We need it led, executed, and sharpened — not reinvented in your image.
• You've only ever served one motion. If you've done pure self-serve or pure enterprise sales-led — but never both at once — this will be a hard job.
• You think customer success means managing a support queue, or you measure your team on activity instead of revenue outcomes.
• Your first instinct is to add headcount. We run lean by design — leverage comes from focus, systems, and AI, not staff.
• You've only ever led co-located teams. Our customers and our team span the globe.

What a realistic week looks like

• A renewal-risk working session with an AM Director, going deep on two save plans.
• An executive sponsor call with a strategic BPO account, then a same-day decision on an escalation you pulled the right people into.
• An expansion pipeline review with the CRO.
• Inspecting health-score movement and cadence adherence across regions — and holding a team lead accountable where it slipped.
• Shipping an agent workflow that flags at-risk accounts a quarter earlier — then teaching the team to build the next one.
• Live collaboration during Eastern Time hours with async updates for teammates in other time zones.
• Reporting NRR, churn, and save rate to the Senior Leadership team with zero fluff.

Your experience

• 8+ years of post-sale leadership in B2B SaaS — Customer Success, Account Management, or equivalent — including 3+ years leading managers and multi-function teams.
• A proven, measurable track record of improving Net Revenue Retention and reducing churn in a growth-stage B2B SaaS company — you know your numbers cold and can walk us through them.
• Owned or co-owned expansion revenue, partnering effectively with sales leadership on account growth.
• Served a global customer base and led distributed remote teams across regions, cultures, and time zones — effective both live and async.
• Operated a hybrid revenue model spanning product-led/self-serve and sales-led motions.
• Hands-on AI builder: you've personally designed and deployed agent workflows and automation in CS or service operations, can name your stack, and can show what it shipped.
• A record of driving disciplined execution of defined playbooks and operating models — you make systems run, not just design them.
• Executive presence and credibility with senior customer stakeholders, including in escalations and renewal-risk situations.
• Comfortable hands-on with CS tooling, CRM, and product usage data. HubSpot experience is a plus.
• Based in North America, with working hours that overlap Eastern Time and the ability to travel 10-20%, including occasional international travel.

Nice to have

• Background in workforce analytics, workforce/talent management, HR tech, or productivity software.
• Experience serving BPO/outsourcing, healthcare, or tech services customers.
• Experience across SMB, mid-market, and strategic/enterprise segments, including digital or scaled CS programs.

How we'll measure success

• Net Revenue Retention — including delivery against an owned expansion number.
• Gross Revenue Retention and churn against baseline.
• Playbook execution quality — engagement plan coverage, cadence adherence, health score accuracy.
• Faster time-to-value and stronger product adoption.
• Save rate and renewal readiness.
• Support quality and resolution across regions.
• More output per person because of the AI systems you've built — and a healthy, productive team that stays.

Why this role

• Own the single biggest lever in our growth plan — with real authority over the outcomes you're measured on.
• Participate in the upside. Competitive comp tied to company outcomes you help generate.
• Report directly to the CEO with a real seat at the leadership table.
• Profitable, growing company — your budget comes from customers, not a burn rate.
• The playbook is built and the teams are in place — you get to make it perform, not clean up a mess.
• Build the AI-first customer success playbook from the front, instead of inheriting someone else's.
• Fully remote and flexible — work with talented people in 30+ countries, and travel to some awesome places.