Senior Director, Sales Systems & Data

Reporting to the Vice President of Revenue Operations, the Senior Director of Sales Systems & Data is accountable for the integrity, scalability, and leverage of all sales systems, revenue data, and go-to-market technology. This role leads teams across Sales Systems, Data Infrastructure, Order Operations, and Go-To-Market Engineering, with end-to-end ownership of revenue data accuracy, seller productivity, and pipeline enablement through technology. The role partners closely with Sales, Finance, FP&A, Legal, Customer Success, and Executive Leadership to ensure revenue operations are accurate, defensible, and scalable as the business grows. This is a full time remote position on our team that may require occasional travel for team or company events.

What You'll Be Doing

• Own Salesforce and the broader sales systems ecosystem as the system of record for bookings, CACV, contract terms, upsells, and renewals, ensuring accurate and auditable revenue data end to end.
• Establish and maintain a durable Sales Source of Truth, including governance, snapshots, and alignment across Salesforce, billing, finance, and downstream systems.
• Lead quarterly and annual CACV refreshes and monthly customer census updates in partnership with FP&A to support forecasting and invoicing accuracy.
• Define and manage the Salesforce and sales systems roadmap, balancing operational stability with strategic enablement.
• Own end-to-end order operations, including review and validation of all new business, upsell, and renewal orders.
• Ensure alignment of sales agreements with pricing governance, company policy, and revenue recognition requirements, partnering closely with Finance, Billing, and Legal.
• Proactively mitigate risk through recurring audits of billable rates, contracts, and opportunity close processes.
• Lead Go-To-Market Engineering to scale pipeline generation and seller productivity through AI, automation, and data-driven execution.
• Own the revenue organization technology stack, including licensing, integrations, ongoing optimization, and approximately $3M in annual vendor operating expense.
• Serve as a senior thought partner to the CRO, VP of Revenue Operations, and Finance leadership, leading high-priority initiatives and building high-performing systems, data, operations, and GTM engineering teams.

What success looks like in this role:

• 97-99% Salesforce invoicing data accuracy by September 1.
• 100% alignment on key revenue metrics with FP&A by the 6th business day of each month.
• Fewer than five systems-driven CACV incidents per quarter with variance of plus or minus one million dollars.
• Vendor operating expense at or below approved annual budget.
• Fewer than three invoicing issues per quarter tied to opportunity closure errors.
• Fifty percent increase in unique prospects engaged per seller.
• Thirty percent reduction in non-revenue-generating activity across sales teams.

What We Expect From You

• 10+ years of experience leading revenue systems, sales operations, data, or GTM technology teams.
• Proven track record owning complex Salesforce and revenue data environments at scale.
• Experience leading multi-team organizations across systems, data, and operational functions.
• Strong executive communication skills with the ability to translate complexity into clarity.
• Deep expertise in Salesforce, revenue data architecture, and GTM technology ecosystems.
• Demonstrated ability to balance strategic leadership with hands-on problem solving.
• Ability to thrive in a fast-paced, high-change environment and lead through ambiguity.

The target base salary range for this position is $188,000 - $216,000 and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, location, internal pay equity, and other relevant business considerations. We review all employee pay and compensation programs annually using Radford Global Compensation Database at minimum to ensure competitive and fair pay.

Benefits provided by Spring Health:

Note: We have even more benefits than listed here and below, your recruiter will provide more in-depth information as you continue in the interview process. Benefits are subject to individual plan requirements and eligibility criteria.

• Health, Dental, Vision benefits start on your first day at Spring. You and your dependents also receive access to One Medical accounts HSA and FSA plans are also available, with Spring contributing up to $1K for HSAs, depending on your plan type.
• Employer sponsored 401(k) match of up to 2% for retirement planning
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents.
• We offer competitive paid time off policies including vacation, sick leave and company holidays.
• At 6 months tenure with Spring, we offer parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a weight management program-based in psychology, that's tailored to your unique needs and goals.
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses.
• Access to Wellhub, which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription
• Access to BrightHorizons, which provides sponsored child care, back-up care, and elder care
• Up to $1,000 Professional Development Reimbursement a year.
• $200 per year donation matching to support your favorite causes.