VP of Customer Success

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.

Our Hiring Approach

🌍 This is a full-time, 100% remote role, giving you the freedom to work from anywhere.

🤝 Equal opportunity employer — we deeply value diversity and inclusion. We welcome applicants of all backgrounds and do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability.

🗺️ We hire globally. Depending on your location, you may join as a full-time employee or contractor. Our Talent Attraction team will walk you through all the details during your first interview.

Who are we?
We’re a global team building the future of workforce analytics, focused on visibility, trust, performance, and growth. Our mission is to empower people and companies thrive in the modern world of work, while giving business leaders the confidence to scale.

We’re a fully remote, async-first company with 150+ team members across 35+ countries. We collaborate across time zones and cultures and value thoughtful, data-informed decision-making. We’re looking for globally minded people who want to help shape the future of work through data, trust, and empowered leadership.

Learn more about us here: https://people.timedoctor.com