Senior Director, GTM Effectiveness

Location: Remote, USA
This role will be posted through 9am et Monday, October 26th, 2026

How You’ll Contribute to Our Mission

At Frontline Education, our vision is clear: Every school thriving. Every community stronger. Our mission is equally important: We transform how schools work, so every educator and student succeeds.

The Senior Director of GTM Effectiveness owns the strategy, standards, and measurement that make sure what Frontline teaches its go-to-market (GTM) teams shows up on customer calls, in implementations, and in the numbers. The role sits in GTM Operations, leads the function through its Director and functional leads, and covers our sellers, our Client Value Partners (CVPs), who manage customer relationships after the sale, and the leaders who coach both. It also includes our Professional Services team, which implements Frontline products and trains district staff, as a smaller part of the role.

We’re ramping a large class of new sellers at the same time we bring a full calendar of product launches to K-12 districts. You’ll define what the field needs to be able to say and do, coach it into practice with sales and client success leaders, and show whether it worked. That includes new seller ramp, launch certification, sales kickoff, and the weekly coaching rhythm that turns training into habits, with Learning and Development and Product Marketing as your partners on the content behind it.

Enablement prepares the team, and effectiveness proves whether the preparation worked. You’re accountable for the second part. You’ll own ramp time, launch certification, scorecard movement on live calls, and launch readiness for Professional Services, and share accountability with Sales and Client Success leaders for conversion and win rate for sellers and retention and expansion for CVPs.

How You’ll Drive Success

Set the strategy and own the operating model

·           Set the multi-year GTM effectiveness strategy and operating model, and tie the annual plan to the hiring plan, launch calendar, and revenue targets.

·           Own the budget for training, tooling, and vendors, including build-versus-buy decisions, and make the business case for each investment.

·           Set the ramp, certification, coaching, and launch-readiness standards for Sales, Client Success, and Professional Services.

·           Advise the VP and leadership team on where field time and enablement investment will move the numbers most.

·           Present effectiveness results and launch readiness to executive leadership, with a recommendation on what to change.

Set the standard for what good looks like

·           Define the selling and account management behaviors we expect by role and by stage, from first meeting through renewal.

·           Turn our sales methodology, including MEDDPICC, into stage-by-stage expectations that managers can coach and Gong can score.

·           Build a GTM maturity model that shows where each team stands today and what the next level requires.

·           Bring outside sales training into our methodology, then certify and coach the skills after the workshop ends.

Own ramp for new sellers and CVPs

·           Own onboarding results for every new seller, SDR, and CVP, from day one to full productivity.

·           Set the onboarding model, with cohorts, checkpoints, knowledge checks, and certification before a new hire carries a full book, and hold the Director accountable for running it.

·           Set the ramp bar for each role, and report progress against it to sales and client success leadership.

·           Keep the program sized to the hiring plan, working with hiring managers and Learning and Development.

·           Hold the team accountable for one current GTM learning hub, so sellers and CVPs have one place to find what they need.

Quarterback every launch in the field

·           Write the field requirement for each major (Tier 1 and Tier 2) launch: the few things a seller or CVP must say and do, and the scorecard questions that will show it.

·           Partner with Product, Product Marketing, and Learning and Development so launch content is built to that requirement and sized to the launch tier.

·           Certify sellers on Tier 1 launches before general availability, using live practice and the Gong AI Trainer.

·           Lead the field program at sales kickoff with Sales leadership and Marketing.

·           Bring a 30, 60, and 90-day read on every major launch to the Launch Readiness Council.

Coach sellers, CVPs, and their managers

·           Coach Sales and Client Success leaders to coach their managers and set the coaching standard the field is held to.

·           Hold Sales and Client Success leaders accountable for a weekly coaching rhythm in which managers coach to the scorecard in their one-on-ones.

·           Set the criteria for targeted coaching, and hold managers accountable for building and acting on a plan for each rep who needs one.

·           Build a library of strong calls, objection handling, and value stories that teams can use with district HR, finance, and student services leaders.

Prove what worked

·           Build the indicators that connect training to results: launch and stage scorecards, trackers, and the dashboards leaders coach from.

·           Read results on a set calendar: ready before launch, in use within 30 days, and winning at 60 and 90 days.

·           Tie coaching and training to conversion, win rate, deal size, cycle time, and ramp for sellers, and to retention and expansion for CVPs.

·           When a number is red, find the cause and coach to it first, and send content back to be fixed only when the pattern points there.

Extend effectiveness to Professional Services

·           Get Professional Services consultants ready for each major launch before customers start implementing it, working with services leadership and Services Operations.

·           Set onboarding checkpoints for new Professional Services hires, and certify them on the products they implement.

·           Coach sellers and Professional Services to the same customer story, so what we promise in the sale matches what the implementation delivers.

Partner across the go-to-market organization

·           Work with Sales, Client Success, and Professional Services leadership on priorities, and give them a clear read on where each team stands.

·           Partner with Revenue Operations and the GTM PMO so process and system changes reach the field with training and a named owner.

·           Agree on intake, priority, and build timelines for GTM content with Learning and Development.

·           Work with Product Marketing on messaging and on what the field needs to win with each launch.

Lead the GTM Effectiveness team

·           Lead a small, senior team that covers indicators and analytics, success enablement, and field coaching.

·           Coach and shape the team as the 2027 launch and hiring plans firm up.

·           Set team goals tied to field results, and report progress to GTM and Sales leadership on a regular schedule.

·           Grow the team’s coaching and analytics skills so the function keeps pace with the business.

Use AI to give every rep more practice and feedback

·           Use the Gong AI Trainer and automated call scoring so every rep gets regular practice and feedback, including the reps a manager doesn’t reach that week.

·           Send managers a weekly AI-generated summary of coaching insights for their team.

·           Put AI practice scenarios in front of sellers and CVPs so they can rehearse a pitch or an objection before the live call.

·           Automate the reporting that shows managers where to coach.

What You Bring to Help Us Grow

·           Ten or more years of progressive experience in sales enablement, sales effectiveness, or sales leadership, including at least five years leading enablement or effectiveness teams and at least three years leading leaders or multiple teams in B2B SaaS.

·           A record of building onboarding programs that shortened ramp, with the data to show it.

·           Experience coaching sellers and frontline sales managers, and setting up a coaching rhythm that managers keep.

·           Fluency in a formal sales methodology such as MEDDPICC, and experience certifying field teams on new products.

·           Hands-on experience with Gong or similar conversation intelligence, including scorecards, trackers, and call libraries.

·           Experience enabling account management and customer success teams on retention and expansion, and professional services teams on delivery.

·           Comfort with data: you build and read dashboards and connect behavior on calls to results.

·           Strong facilitation skills, and executive communication that leads with the finding and the recommendation.

·           Experience standing up an enablement or effectiveness function is a plus.

·           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

·           Coach First. You’d rather sit in on a call than send another deck.

·           Outcome Owner. You judge your work by what changes on calls and in the numbers.

·           Calm Orchestrator. You keep many launches and many teams on one plan, and you do it without drama.

·           Credibility With the Field. You know what good selling looks like, and sellers and managers trust your read.

·           Bias for Speed. Launch dates hold, so you deliver on the business’s timeline.

AI-First Competencies

The Senior Director of GTM Effectiveness:

·           Uses AI daily to review calls, spot coaching patterns, and prepare manager briefs.

·           Uses AI practice tools so every rep can rehearse before a live conversation.

·           Looks first at whether a coaching insight can be automated and delivered where reps already work.

·           Shares working AI practices with field leaders so the capability compounds.

Our Mission, Our People, Our Purpose

At Frontline Education, we’re reimagining what’s possible by becoming an AI-first organization, transforming how we think, work, and serve the educators who shape our schools every day. By using AI in thoughtful, practical ways, we’re creating tools that help educators save time, gain insights, and focus more on what matters most — their students.

As part of our team, you’ll be expected and empowered to build and apply AI skillsets that grow with you, because at Frontline Education, technology amplifies what matters most: the human drive to learn, improve, and make a difference.

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.

Inclusion, Belonging & Equal Opportunity

Frontline Education is an equal opportunity/affirmative action employer. We aspire to have an inclusive workplace and strongly encourage suitably qualified applicants from a wide range of backgrounds to apply and join our team.

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Interview Process & Data Privacy

As part of our interview process, Frontline uses video conferencing tools that include photo capture and may include automated transcription features. A screenshot or photo will be taken at the start of the interview for internal identification and record-keeping purposes only, and transcription may be used to support notetaking and evaluation consistency. These materials are used solely by our recruiting and hiring teams, stored securely, and not shared outside the hiring process. Candidates may opt out of the transcription at any time by notifying their recruiter in advance. Frontline processes this information in accordance with applicable data privacy laws and only for legitimate business purposes related to recruitment and hiring.