TRAILS

• Serve as a strategic partner to the CEO, anticipating needs and removing friction before it surfaces • Manage the CEO's priorities, follow-up items, and key decisions — ensuring nothing gets lost • Build and maintain organizational systems that support the leadership team's effectiveness • Automation & Systems Design — this person builds workflows — in service of people, not instead of them and reduces repetitive tasks. • Track open action items, decisions, and commitments across the leadership team and drive accountability for follow-through • Own the design, facilitation, and follow-up for all leadership team meetings — setting agendas, running the meeting rhythm, and capturing clear next steps • Manage meeting cadences across the organization to ensure time is used intentionally and productively • Facilitate working sessions that drive alignment and decisions, not just status updates • Project-manage the development of all high-stakes decks, including board presentations, all-staff meetings, and leadership team materials • Collaborate with leaders and stakeholders to gather content, ensure narrative clarity, and manage timelines from first draft through final delivery • Design and maintain the organization's systems for tracking data, OKRs, and key metrics across teams • Build and steward documentation systems that keep institutional knowledge organized, accessible, and up to date • Lead end-to-end planning and execution for staff events (1-2 times per year), and leadership retreats (2-3 times a year) — from venue selection and vendor coordination to run-of-show and post-event wrap-up • Anticipate and resolve logistical challenges before they become problems

• Own and exceed annual new annual recurring revenue and renewal targets for the K–12 segment • Build and manage a healthy, forecastable pipeline using a consultative sales approach • Lead complex, multi-stakeholder deals involving curriculum directors, principals, school psychologists, IT, and district finance • Navigate RFP, procurement, and approval processes common to public school districts • Cultivate relationships with state education agencies, mental health coalitions, and intermediary organizations • Identify and pursue grant-funded opportunities (e.g., ESSER, Title IV, state mental health grants) where districts use public funding for our product • Represent the organization at key K–12 and mental health conferences • Partner on K–12 campaign strategy, event presence (e.g., NASN, ASCA, SXSWedu), and inbound lead quality • Work closely with Customer Success teammates to ensure smooth handoffs and strong retention in your accounts • Provide structured feedback to Product on school-specific needs, objections, and competitive dynamics • Develop and refine sales playbooks, messaging, and objection-handling frameworks tailored to district buyers • Support TRAILS team with all hands on deck events as needed and other team initiatives

This description is a summary of our understanding of the job description. Click on 'Apply' button to find out more. Role Description We are seeking a mission-driven Director of Growth to lead and grow our K–12 go-to-market efforts. In this role, you will drive revenue by building relationships with district administrators, school counselors, and state-level decision-makers who are actively investing in student mental health infrastructure. You will own the full sales cycle from prospecting to close, and help shape the sales strategy for a product that genuinely improves student wellbeing. This is a high-impact, high-visibility position for someone who deeply understands the rhythms of K–12 procurement, is passionate about mental health in schools, and knows how to build a repeatable, scalable sales motion in a mission-oriented environment. Responsibilities - Revenue & Pipeline Ownership (40%) - Own and exceed annual new annual recurring revenue and renewal targets for the K–12 segment. - Build and manage a healthy, forecastable pipeline using a consultative sales approach. - Lead complex, multi-stakeholder deals involving curriculum directors, principals, school psychologists, IT, and district finance. - Navigate RFP, procurement, and approval processes common to public school districts. - Market Development (30%) - Cultivate relationships with state education agencies, mental health coalitions, and intermediary organizations. - Identify and pursue grant-funded opportunities (e.g., ESSER, Title IV, state mental health grants) where districts use public funding for our product. - Represent the organization at key K–12 and mental health conferences. - Strategy & Cross-functional Collaboration (20%) - Partner on K–12 campaign strategy, event presence (e.g., NASN, ASCA, SXSWedu), and inbound lead quality. - Work closely with Customer Success teammates to ensure smooth handoffs and strong retention in your accounts. - Provide structured feedback to Product on school-specific needs, objections, and competitive dynamics. - Develop and refine sales playbooks, messaging, and objection-handling frameworks tailored to district buyers. - Team responsibilities (10%) - Attend all staff meetings and retreats, workgroups and other relevant TRAILS meetings as necessary. - Support TRAILS team with all hands on deck events as needed and other team initiatives. Qualifications - 5–8+ years of B2B sales experience, with at least 3 years focused on selling into K–12 school districts. - Demonstrated track record of meeting or exceeding quota in K–12 EdTech or adjacent markets (e.g., SEL, school counseling tools, student wellness platforms). - 2+ years in a sales leadership or management role. - Experience managing complex, multi-stakeholder sales cycles of 3–9 months. - Familiarity with grant-funded procurement processes in public education is a strong plus. Requirements - Genuine belief in the mission: that every student deserves access to mental health support. - Deep understanding of the K–12 buyer landscape — who influences, who decides, and how budgets are allocated. - Ability to speak credibly to school counselors, mental health coordinators, and district administrators about student wellbeing outcomes. - Strong pipeline management discipline using CRM tools (Salesforce or HubSpot preferred). - Excellent communicator — with both internal teams and external partners. - Comfortable navigating ambiguity in a growing startup or scale-up environment. - Data-informed decision maker who can zoom out strategically and zoom in on individual deals. - Resilient and adaptable — K–12 sales cycles are long and procurement can be unpredictable. - Collaborative leader who believes in building and actively participating in a strong team culture. Benefits - The salary range for this role is $127,155 - $134,219. - TRAILS offers a comprehensive benefits package including medical, dental, and vision. - 403B with a safe harbor match. - Short and long term disability. - A generous holiday and paid time off package. Application Notes Our job descriptions reflect TRAILS’ assignment of essential functions and qualifications of the role. Nothing herein restricts management's right to assign, reassign or eliminate duties and responsibilities to this role at any time. We are only considering applicants who are legally authorized to work in the United States. Please note that TRAILS employees may be required to undergo a background check. Findings do not automatically exclude candidates from the hiring process, but will be taken into consideration. Our Commitment to Diversity, Equity, & Inclusion Addressing inequities in access to evidence-based mental health care is intrinsic to the TRAILS mission. The intentionality behind this approach is woven into everything we do at TRAILS, resulting in a staff-wide commitment to diversity, equity and inclusion for all facets of our program. If this commitment is something to which you could positively contribute, we encourage you to apply, particularly if your voice represents a historically excluded perspective. TRAILS is an “at-will” and equal opportunity employer. Applicants and employees shall not be discriminated against because of race, religion, sex, national origin, ethnicity, age, mental or physical disability, sexual orientation, gender (including pregnancy and gender expression) identity, color, marital status, veteran status, medical condition, or any other classification protected by federal, state, or local law or ordinance.