Head of Enterprise Accounts

Trestle is transforming the construction industry by solving long-standing challenges in communication and data connectivity. Our mission is to improve collaboration and streamline workflows, enabling projects to be completed faster and more efficiently. We are a fast-paced, mission-driven team that thrives on tackling challenges and driving innovation. If you're looking for a dynamic environment with significant growth opportunities and want to help reshape how the world builds, Trestle is the place for you. About the Role: Trestle's marquee enterprise accounts, general contractors managing thousands of vendors and hundreds of millions in subcontracted risk, are expanding. We're looking for a Head of Enterprise Accounts to own these relationships from start to finish: be the point person for our largest customers, translate their needs into product requirements, and make sure Trestle never gets outgrown by the accounts that matter most. This is a senior, standalone individual contributor role reporting directly to the CEO. You'll operate at the executive level with VPs of Risk, Directors of Procurement, EVPs of Operations, and CFOs at some of the largest general contractors in the country, often without a founder in the room. You'll also be the main link between what customers need and what engineering builds, working directly with our product and engineering team to scope and prioritize their asks. This is not a new business sales role. You won't be prospecting or closing net-new logos. Your job is to be the trusted steward of relationships that already exist, and to grow them responsibly over time, through renewals, usage expansions, and new modules, as the account's needs evolve. Compensation reflects this: it is weighted toward relationship management and account health, with account growth as a real but secondary component. We're open to two different backgrounds for this role, and we care more about the level of experience than the specific industry it came from. One path is a background in enterprise software account management, running QBRs, tracking account health, and managing renewals and expansion for large customers. The other path is a senior construction professional, such as a senior project manager or similar, who has managed both vendor-facing and owner-facing relationships at a large general contractor and is ready to bring that judgment into a software company. Either path works, as long as the seniority and stakeholder management experience is real: this role is not a fit for someone early in their career in either construction or software. Key Responsibilities: Own Marquee Account Relationships: Serve as the primary point of contact for Trestle's largest enterprise accounts post-close, including champions and executive sponsors on the risk, procurement, and operations side. Executive-Level Trust: Operate independently in rooms with CFOs, VPs of Risk, and EVPs. Build the kind of credibility that keeps renewals and expansions on track without constant founder involvement. Translate Customer Needs into Product Requirements: Take customer concerns, requests, and pain points directly to the product team and engineering, scoping vague asks into requirements that can actually be built. Account Health and Retention: Build and run account health tracking, proactively surfacing risk before it becomes a churn or escalation event. Run Structured QBRs: Establish a cadence of business reviews with each marquee account, demonstrating value delivered and aligning on what's next. Own Renewal and Responsible Expansion: Drive renewal conversations and identify legitimate expansion opportunities (vendor count, additional modules, multi-year terms) as an extension of good account management, not a sales motion. Build the Playbook: There is no enterprise account management function at Trestle yet. You will build the QBR cadence, escalation paths, and account health scoring from scratch. Cross-Functional Collaboration: Work closely with engineering, product, and the CEO so marquee account commitments are realistic and get delivered on. Qualifications: Must-Haves, in priority order Fast domain pickup: not required to already know construction, but must show the ability to absorb technical/compliance concepts (like EMR, COI, subcontractor default insurance) quickly and explain them back credibly. This will be tested live in the interview process, not assumed from a resume. Real, senior-level relationship management experience: either hands‑on reps running QBRs, account health scoring, and renewal/expansion conversations in enterprise software, or equivalent senior-level experience managing both vendor-facing and owner-facing relationships at a large general contractor. Either path is valid, but the experience must be senior and real, not adjacent or early-career. Credibility with senior, skeptical stakeholders in a specialized or technical vertical: proven ability to earn trust with executives (CFOs, VPs, senior operators) in a domain the candidate didn't start out knowing. Experience in another technical vertical (healthcare, insurance, fintech, or similar) is a strong signal even without construction background. Technical translation instinct: able to take a vague customer complaint and dig into the underlying workflow and root cause, rather than staying at the surface level. This will be tested with a live role‑play in the interview. Proactive escalation instinct: a track record of surfacing problems before a customer has to escalate over their head, and adjusting after being caught flat‑footed in the past. This will be probed directly in reference checks. Ownership and builder mentality: comfortable building process, QBR cadence, and escalation paths from scratch in an early‑stage, ambiguous environment, since none of this exists at Trestle yet. Fluent English: native‑level proficiency. Preferred For candidates coming from construction rather than software: senior-level experience such as a senior project manager or above, with a track record of managing both vendor-facing and owner-facing relationships at a large general contractor. This is not a fit for project engineers or early‑career project managers. Existing relationships with, or direct account management experience at, ENR Top 100 general contractors. Experience selling or supporting SDI (subcontractor default insurance) or surety‑adjacent products. Background in insurance brokerage or risk management channels. What Success Looks Like: At 1 Month: Complete onboarding and hold introductory calls with every existing champion and executive sponsor on marquee accounts. Establish an account health tracker and a QBR cadence for each marquee account. Shadow at least one live customer escalation or product request from intake through engineering handoff. At 3 Months: Run the first full QBR cycle across all marquee accounts. Have a documented escalation path and a working relationship with engineering for translating account requests into scoped work. Identify at least one expansion or upsell opportunity on an existing account. At 6 Months and Beyond: Marquee accounts show measurable improvement in NRR, logo retention, and time‑to‑resolution on escalations. The account management playbook (QBR structure, health scoring, escalation paths) is documented and repeatable for future hires. Serve as someone the CEO can trust to represent Trestle in high‑stakes rooms without needing oversight. What We Offer: Competitive base salary, which makes up the majority of total compensation, reflecting that this is a relationship and account management role, not a sales role. An account growth bonus on top of base, paid quarterly or semi‑annually, tied to account retention and responsible expansion revenue on your accounts. This is not a commission structure and is not paid on new business. Meaningful, early‑employee‑level equity. Comprehensive medical, vision, and dental health plans. Flexible vacation policy. A foundational role in building Trestle's enterprise account function from the ground up. A dynamic work environment where you'll never be bored! This role requires full-time, in‑person work at our New York City office for the first 3 to 6 months. Given the trust and coordination this position requires early on, including joint account calls and real‑time coaching, close in‑person collaboration with the CEO is essential during the ramp period. After that, the role moves to our standard policy of on‑site three days per week with the option to work remotely on the remaining days. Commitment to Equal Employment Opportunity: Trestle is an equal opportunities employer, committed to building an integrative culture where everyone feels welcomed and supported. We embrace uniqueness and understand that our diverse, values‑driven culture makes us stronger. This commitment extends to all aspects of the employment relationship, including recruiting, interviewing, selection, hiring, transfers, promotions, training, terminations, working conditions, compensation, and benefits. #J-18808-Ljbffr MetaProp