VP of Customer Success

Time Doctor • New York, NY

2d • Remote

About The Position

Time Doctor is seeking a VP of Customer Success to lead retention for over 10,000 global customers. This role involves managing a hybrid product-led and sales-led business, with a focus on making an existing Customer Success Playbook perform and building an AI-first function from the ground up. The VP will report to the CEO, collaborate with the CRO and revenue team, and oversee Account Management, Support, and Solutions as a unified post-sale organization. The core responsibility is to maintain and grow customer revenue through renewals, saves, and expansions, leveraging a rebuilt CS Playbook and an AI-first operating model. This is a hands-on role requiring disciplined execution, data-driven refinement, and personal involvement in building AI agent workflows.

Requirements

• 8+ years of post-sale leadership experience in B2B SaaS (Customer Success, Account Management, or equivalent).
• 3+ years of experience leading managers and multi-function teams.
• Proven, measurable track record of improving Net Revenue Retention and reducing churn in a growth-stage B2B SaaS company.
• Experience owning or co-owning expansion revenue and partnering with sales leadership on account growth.
• Experience serving a global customer base and leading distributed remote teams across regions, cultures, and time zones.
• Experience operating a hybrid revenue model spanning product-led/self-serve and sales-led motions.
• Hands-on AI builder: personally designed and deployed agent workflows and automation in CS or service operations.
• Record of driving disciplined execution of defined playbooks and operating models.
• Executive presence and credibility with senior customer stakeholders, including in escalations and renewal-risk situations.
• Comfortable with CS tooling, CRM, and product usage data (HubSpot experience is a plus).
• Based in North America, with working hours overlapping Eastern Time.
• Ability to travel 10-20%, including occasional international travel.

Nice To Haves

• 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.

Responsibilities

• Own Net Revenue Retention (NRR) across the installed base, including Gross Revenue Retention (GRR) and churn reduction.
• Drive expansion revenue through upsells, cross-sells, and seat growth in partnership with the CRO and revenue team.
• Ensure disciplined and consistent execution of the CS Playbook across all pods and regions.
• Provide executive sponsorship for strategic customers, managing senior stakeholder relationships and high-risk escalations.
• Oversee onboarding and time-to-value through the Solutions team to ensure rapid customer value realization.
• Manage and improve the support experience, focusing on service quality, responsiveness, and effectiveness.
• Develop and implement an AI-first operating model, embedding agents and automation into daily CS operations.
• Hire, develop, and lead team leads and individual contributors across Account Management, Support, and Solutions in multiple time zones.
• Foster AI fluency within the team, enabling them to build and scale their own agentic workflows.
• Collaborate with the CRO and revenue team on expansion pipeline visibility and smooth handoffs.
• Refine the CS system with data as the company scales.
• Report on NRR, churn, and save rates to the Senior Leadership team.

Benefits

• Competitive compensation tied to company outcomes.
• Opportunity to report directly to the CEO and have a seat at the leadership table.
• Work for a profitable, growing company.
• Opportunity to build the AI-first customer success playbook.
• Fully remote and flexible work environment.
• Opportunity to collaborate with talented people globally.
• Travel opportunities.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed