Head of Customer Success

About the role

What we're doing

Owning a home is a foundational part of building financial security and wealth in America. However, the tools and technology that support homeownership are antiquated, dependent on things like fax machines, handwritten documentation, and hours of manual review.

We're here to change it.

Vesta is the next-generation system of record to power the multi-trillion mortgage market. We believe that we are overdue for a core transformation - that in order to build a fully automated process and fully digital customer journeys, lenders will have to adopt a system of record platform that is modern, open, and orchestrated by best-in-class software workflows.

Who you are

• You are deeply curious about how businesses operate.
• You enjoy understanding workflows, incentives, constraints, and organizational dynamics - especially within operationally intensive industries.
• You thrive in early-stage environments where ambiguity is high and ownership is real.

• You think in terms of outcomes, not activities. You care about measurable impact and can clearly articulate the value your product delivers.
• You are comfortable partnering with senior stakeholders and can build trust with operators, executives, and cross-functional leaders alike.
• You’re calm under pressure and effective at coordinating internal teams when challenges arise, serving as a structured and accountable escalation point.
• You are highly organized and process-oriented, with the ability to build playbooks and systems from scratch.
• You can balance proactive strategic engagement with reactive issue management without losing momentum.
• You are collaborative by default - able to partner closely with Sales on renewals, with Product on feedback loops, and with Implementation on smooth customer transitions.

About the role

Vesta is hiring a Head of Customer Success team member to own and build the post-implementation customer experience. This is a foundational, high-impact role responsible for ensuring our customers realize meaningful, measurable value from Vesta long after go-live.

Early on, you’ll own several of our most strategic relationships, our largest and most complex accounts, and serve as their primary strategic partner. Your focus will be driving adoption, deepening engagement with new functionality, reinforcing best practices, and ensuring Vesta evolves alongside our customers’ businesses. While Sales will own commercial renewals, you will play a critical role in retention by maintaining strong executive relationships and ensuring customers consistently see operational impact.

You’ll build the function. You’re the first hire in this org, and you’ll set its foundation: engagement models, success metrics, health signals, feedback loops to Product, and the operating cadence that scales as we grow. You’ll hire, shape, and manage the first individual contributors on your team, and you’ll decide how accounts are segmented and distributed as the book grows.

You and your team will act as the quarterbacks for our customer accounts - coordinating cross-functionally when issues arise, acting as a senior escalation point, advocating for customers internally, and ensuring alignment between Product, Support, Implementation, and Sales.

• This role requires both strategic thinking and operational rigor - someone who can zoom out to shape the future of Customer Success at Vesta while staying close to the details that drive customer outcomes.
• What this role is not
• This is not a commercial role. You will not own or negotiate renewals, upsells, expansions, or pricing. These activities sit under the Head of Revenue, and it is the Customer Success org's mandate to surface risk and opportunity signals, and hand them off.
• This is not a support role. Day to day issues and ticket resolution are owned by the Support org. Customer success is not a second support queue or a way for our clients to skip the line, though you should expect escalations from time to time.
• This role does not own implementation or project management. Implementation Managers lead delivery and launch; Customer Success owns the post-go-live strategic relationship, adoption, and value realization.

This role is not purely operational or programmatic. Systems, metrics, and playbooks matter, but the role requires direct, credible engagement with sophisticated lender stakeholders and strong judgment in ambiguous, cross-functional situations.You’ve built a Customer Success function before - ideally from zero - and you know what it takes to go from “no playbook” to a team that runs on its own. You’ve done the first-hire, first-process, first-metric work and you’re energized by doing it again.

You’re credible with executives. You can walk into a strategic account, build trust with operators and C-level stakeholders alike, and be the person they call when something matters.

You build systems. Playbooks, engagement models, health scoring, operating cadence - you’ve designed these from scratch and know which ones actually matter at this stage versus later.

You’re a hands-on leader. You’ll hire and develop the team, but you’ll also carry the most strategic accounts yourself, and you’re comfortable doing both at once for a while.

Benefits and Perks

• Robust medical, vision, & dental coverage (~100% of employee premiums covered)
• FSA plan offering
• 401(K) plan offering
• Meaningful parental leave - 16 weeks fully paid for all new parents, birthing & non-birthing parents (applies to adoptions as well!)
• Remote-first culture with a physical hub in the Bay Area & New York!
• Generous Work From Anywhere & Wellness Benefits
• Monthly cell & wifi stipend
• Monthly Doordash benefits
• Open & encouraged flexible time off
• Company offsites to get to know the team!

Our cash compensation amount for this role is targeted at $200,000 - $250,000/yr. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.