Description Senior Director, Revenue Operations
Location: Remote, USA
This role will be posted until 9am ET on 10/27/2026.
The Senior Director of Revenue Operations owns the revenue operating model behind how every Frontline sale and renewal gets quoted, booked, renewed, and reported, and is accountable to the Vice President, GTM Operations for the policy, systems, and forecast integrity behind Frontline's new business and renewal revenue across all products and K-12 district customers. The role sits in GTM Operations and leads two functions through their leaders: a Revenue Operations service desk that covers revenue administration, Salesforce and Gong support, marketing operations, and revenue automation, and a Deal Desk that runs renewals and responds to district RFPs. You will set the strategy, annual plan, and budget for both, and act as a trusted advisor to Sales, Client Success, and Finance leadership.
You'll partner with Sales, Client Success, Marketing, Finance, and our Systems Administration and Business Intelligence team. The first priority is the renewal process. Most K-12 renewals come due around the July 1 fiscal year, so outreach has to start months ahead, offer customers simple choices on term and services, give our Client Value Partners (CVPs) the context they need, and give leadership a renewal forecast it can trust. You'll also lead the business side of Frontline's move from Salesforce CPQ to Revenue Cloud, and keep quoting, ordering, and reporting ready for a full 2027 launch calendar.
In this role, you'll move Revenue Operations from answering requests to spotting problems first and fixing the cause. You'll be measured by request turnaround, the share of repeat work the team retires, renewal timeliness and forecast accuracy, and how early sales and success leaders bring you into their decisions.
How You'll Drive SuccessSet the strategy and own the operating model- Set the multi-year Revenue Operations strategy and roadmap, and translate GTM priorities into an annual operating plan, capacity model, and budget.
- Own the revenue technology roadmap and spend across Salesforce, Gong, and adjacent tools, including build-versus-buy and vendor decisions.
- Set policy for quoting, discounting, pricing approval, booking, and renewal terms, and hold final authority on the revenue definitions used for company reporting.
- Advise Sales, Client Success, and Finance executives on pricing and packaging, territory and compensation design, and renewal strategy.
- Present forecast, renewal, and operational performance to executive leadership, and recommend the actions to take.
Lead the Revenue Operations service desk• Own one front door for GTM requests, including Salesforce and Gong cases, reports, access, and process questions from every customer-facing team.
• Set the service model for the desk, including severity, priority, and service levels for each request type, and hold its leaders accountable for results.
• Sort case volume by type and root cause, then retire repeat requests with standard reports, automation, and self-service.
• Protect time for improvement work so the team fixes the system while it keeps the lights on.
• Plan capacity ahead of known spikes, such as new seller cohorts, product launches, and repackaging work.
Own revenue administration• Set the governance model for territory assignment, account ownership, quota, and compensation plan administration, and partner with Sales leadership and Finance on annual plan design.
• Own pricing and packaging governance, including the price book, SKU catalog, quoting standards, discount policy, and the approval routing behind them.
• Run marketing operations and the lead process with Marketing, from capture through routing and conversion.
• Ensure hardware and training orders move from request through fulfillment within defined service levels.
Build the Deal Desk for renewals and RFPs• Stand up the Deal Desk as one team for renewals and proposals, with clear roles, intake, service levels, and reporting.
• Redesign the renewal process from notice to signature to invoice, including timing, price increase rules, multi-year options, and add-on offers.
• Move customers to a click-to-renew experience where they choose a term and add services without waiting on a manual quote.
• Keep CVPs in the customer conversation while the Deal Desk runs the process, the paperwork, and the renewal forecast.
• Bring discipline to district RFPs: a bid or no-bid standard based on whether our team was engaged before the RFP posted, tracking from intake to award, and AI-assisted drafting from an approved answer library.
Lead the business side of the move to Revenue Cloud• Define how quoting, ordering, amendments, and renewals should work in the future state, and hold the build to it.
• Partner with Systems Administration, Finance, and the GTM PMO on design, data migration, testing, and cutover.
• Use the move to retire today's workarounds, including hand-built order forms and one-off repackaging.
• Keep selling and renewing on track through the transition, with a plan for the extra case volume it creates.
Make every launch ready to sell• Represent Revenue Operations in the product launch process, with the authority to hold a launch that isn't ready to sell.
• Confirm that SKUs, pricing, quoting, and ordering are live before a product goes to market.
• Plan the territory, compensation, and reporting changes each new product requires.
• Work with the GTM PMO and GTM Effectiveness so systems, process, and field readiness land on the same date.
Turn revenue data into early warnings• Set data quality standards for account, contact, and opportunity data, with validation that stops bad data at entry.
• Hold one set of revenue definitions, including gross and net bookings, pipeline, and renewal outcomes, across Salesforce, Gong, and leadership dashboards.
• Build automated alerts for large pipeline swings, slipping close dates, renewals at risk, and data gaps, and route each one to the leader who can act on it.
• Bring sales and client success leaders a point of view on what the data shows, why it matters, and what to change.
• Put Gong, Salesforce, and product usage signals in front of the people who manage each account.
Lead and develop the Revenue Operations team• Assess the team's structure, roles, and skills, and shape it around the work the business needs next.
• Hire, coach, and develop leaders who can run their areas without escalation.
• Set goals and service levels for each team, and review results on a regular schedule.
• Build a team habit of fixing root causes and writing down how the work gets done.
Use AI to take repeat work off the team• Apply AI agents and automation to case triage, RFP drafting, renewal outreach, and data cleanup.
• Automate the recurring reports and data preparation that consume team hours today.
• Pilot one use case at a time, measure the result, and expand what works.
• Build AI fluency into daily work so the team spends its time on judgment calls.
What You Bring to Help Us Grow• Twelve or more years of progressive experience in revenue operations, sales operations, or deal desk roles, including at least five years leading teams and at least three years leading managers or multiple teams.
• Experience running a renewals or deal desk function in B2B SaaS, including pricing, quoting, and contract processes.
• Deep Salesforce experience across Sales Cloud and CPQ, including at least one quote-to-cash redesign or migration. Revenue Cloud experience is a plus.
• Experience designing and governing territories, quotas, and compensation plans in partnership with Sales and Finance.
• Hands-on experience with Gong or similar revenue intelligence and automation tools.
• Experience leading RFP or proposal teams, ideally in public sector or education markets.
• A record of moving an operations team from reactive to proactive, with turnaround and case volume data to show for it.
• Executive communication that leads with the recommendation and the data behind it.
• Experience in SaaS, and in EdTech or K-12 specifically, is preferred.
• A bachelor's degree or equivalent professional experience.
What You'll Need to Thrive• Operator With a Point of View. You see the pattern behind the requests and fix the root cause.
• Calm Under Load. When launches, new sellers, and renewal season land at the same time, you set the priorities and keep the team moving.
• Systems Thinking. You know how a change to a quote, a field, or a SKU shows up in billing, in reporting, and in a customer's inbox.
• Bias for Closure. You finish the cutover, retire the workaround, and close the loop.
• Trusted Partner. Sales, Client Success, and Finance bring you problems early because you solve them.
AI-First CompetenciesThe Senior Director of Revenue Operations:
• Uses AI daily to triage requests, draft RFP responses, and prepare pipeline and renewal reporting.
• Looks first at whether a workflow can be automated before adding headcount or hours to it.
• Applies AI to find patterns across cases, calls, and renewals, and turns them into a short list of decisions.
• Shares working AI practices across GTM Operations so the capability compounds.
How We Support Growth, Balance, and Well-Being• Personalized Time Off: Take time when it's needed most - whether that's a family vacation, a reset day, or simply time to rest and refocus.
• Paid Sick Time: Separate, dedicated sick leave to care for yourself or loved ones.
• Volunteer Time Off: Paid time to give back and support causes that matter to you.
• Ten Paid Holidays: Enjoy meaningful moments and traditions throughout the year.
• Our Philosophy: We believe time away from work helps you bring your best self to it.
Continuous Learning and Growth• World-Class Learning Access: Explore thousands of on-demand courses through platforms like LinkedIn Learning.
• Leadership & Technical Skill Building: Develop new capabilities and chart your own professional path.
• AI Empowerment: Use OpenAI tools to build fluency with emerging technology and harness AI as a creative partner for innovation and problem-solving.
• Tuition Reimbursement: Invest in formal education to advance your skills and career.
• Ongoing Learning Culture: Participate in company-led webinars on AI, inclusion, and industry trends - designed to inspire curiosity and continuous improvement.
Health, Happiness, and Purpose• Wellness Initiatives: Company-sponsored programs that support physical, mental, and emotional well-being.
• Employee Assistance Program (EAP): Confidential support for you and your family's needs.
• Comprehensive Benefits: Health and financial benefits that support your happiness and future.
• A Culture That Cares: At Frontline Education, we want every team member to learn, grow, and thrive - personally, professionally, and purposefully.
Compensation & Benefits• Base salary range of $170,000-$195,000 per year. This role is also eligible for variable compensation under the company's incentive plan, subject to plan terms. Placement within the range depends on experience, skills, and location.
• 401(k) with company match and Employee Stock Purchase Plan (ESPP).
• Comprehensive medical, dental, vision, and wellness benefits.
• Personalized PTO and tuition reimbursement for eligible programs and coursework.
