VP of Customer Success

• Location: Remote, New York, New York, United States
• Employment type: Full-time
• Remote work mention: 100% remote role, fully remote and flexible

Job description

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; execution is your craft.
• Today’s AI landscape energizes you; it doesn’t scare you. You "nerd out" on agents and automation — you build first, delegate second.
• Entrepreneurial and scrappy: you deliver results without waiting for the perfect budget or team size.
• You’re competitive, hungry, coachable — you’ve been coached; you seek out coaches; 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 driving upsell cross-sell seat growth in partnership with CRO/revenue team; shared pipeline visibility; clean handoffs.
• Playbook execution: Disciplined consistent execution of CS Playbook across pods/regions — segmentation engagement statuses/plans health scoring EBRs weekly/monthly/quarterly cadence refined with data.
• Key accounts: Executive sponsorship of strategic customers; personally own senior stakeholder relationships; step into high-risk renewals/escalations; drive fast decisions.
• Onboarding/time-to-value: Implementation/early lifecycle outcomes through Solutions team so customers see value fast/stay.
• Support experience: Service quality responsiveness effectiveness across regions/segments.
• AI-first operating model: Agents/automation embedded daily CS operations—risk detection customer coverage EBR prep support responsiveness reporting—lean team outproduces big one.
• Team: Hire develop lead team leads/ICs across Account Management Support Solutions multiple time zones grow AI fluency build scale agentic workflows.

This role is NOT for you if…

• Manage retention from dashboard don’t like calendar full customer calls (hands-on role).
• "AI experience" means team uses ChatGPT sometimes; need someone who built/orchestrated agent workflows delivering real outcomes.
• Need to design own process to succeed (playbook built).
• Only served one motion (pure self-serve or pure enterprise sales-led but never both).
• Think customer success means managing support queue or measure activity instead of revenue outcomes.
• First instinct add headcount (run lean by design leverage focus systems AI not staff).
• Only led co-located teams (customers/team span globe).

Job requirements

What a realistic week looks like Renewal-risk working session AM Director deep on two save plans; executive sponsor call strategic BPO account same-day decision escalation pulled right people into; expansion pipeline review CRO; inspecting health-score movement cadence adherence regions holding team lead accountable where slipped; shipping agent workflow flags at-risk accounts quarter earlier teaching team build next one; live collaboration Eastern Time hours async updates teammates other time zones; reporting NRR churn save rate Senior Leadership zero fluff. Your experience

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

Nice to have

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

How we’ll measure success

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

Why this role

Own single biggest lever growth plan real authority outcomes measured on Participate upside competitive comp tied company outcomes help generate Report directly CEO real seat leadership table Profitable growing company budget comes customers not burn rate Playbook built teams in place make perform not clean mess Build AI-first customer success playbook front instead inheriting someone else’s Fully remote flexible work talented people 30+ countries travel some awesome places