At Trunk Tools, we’re the leading AI company revolutionizing construction, the second-largest industry on earth. We recently raised a $40M Series B led by Insight Partners, bringing our total funding to $70M from top-tier investors including Redpoint and Innovation Endeavors. This new round is fueling our next phase of growth as we scale AI agents across the jobsite. Our mission is to build the future of construction through intelligent automation. Despite being a $13+ trillion industry, construction still runs largely on analog processes, we’re changing that by embedding AI directly into field operations. Founded by builders and technologists (Stanford, MIT), our team has delivered software used by over 140,000 field professionals, impacting millions of users and contributing to $10B+ in built projects. Many of us come from the field ourselves, giving us a deep understanding of the industry’s unique challenges. After years of building the “brain” of construction, we’re now launching production-ready AI agents, starting with intelligent document processing and Q&A, and rapidly expanding into core operational workflows. Our team has doubled in the past year, and with 65+ employees (25+ engineers), we’re scaling fast and entering a period of hypergrowth. This is a rare opportunity to join at an inflection point. We are seeking a Director of Revenue Operations to build, lead, and optimize our Revenue Operations function. This individual will act as a player-coach: rolling up their sleeves to solve problems directly, while also building and guiding a small but high-performing team. The ideal candidate is deeply metrics-driven and an AI power user, leveraging advanced tools to accelerate productivity, streamline processes, and drive measurable results across our go-to-market (GTM) organization. Key Responsibilities - Strategy & Leadership - Define and execute the overall Revenue Operations strategy to support aggressive growth targets. - Serve as a thought partner to Sales, Marketing, Customer Success, and Finance leadership. - Lead, coach, and develop a team of RevOps professionals while remaining hands-on. - Process Optimization & Enablement - Implement AI-driven solutions to optimize workflows, reporting, forecasting, and pipeline management. - Build scalable processes across the customer lifecycle to reduce friction and increase efficiency. - Partner with GTM leaders to ensure operational alignment and data-driven decision-making. - Data, Analytics, & Metrics - Establish, track, and report on KPIs across sales, marketing, and customer success. - Drive a culture of accountability with clear, actionable dashboards and reporting. - Continuously identify opportunities for process improvements using AI and automation. - Technology & Tools - Own and optimize the revenue tech stack (CRM, marketing automation, analytics tools, etc.). - Evaluate and implement new tools, particularly AI-driven solutions, to improve productivity. Qualifications - 8+ years in Revenue Operations, Sales Operations, or a related GTM operations role, with at least 3+ years in leadership. - Proven track record of implementing AI/automation solutions to drive productivity and growth. - Exceptional analytical skills; obsessed with metrics, KPIs, and data integrity. - Strong communication and leadership skills; ability to influence across departments. - Hands-on experience with modern GTM tools (Salesforce, HubSpot, Gong, etc.) and AI platforms. - Experience in construction technology, SaaS, or related B2B industries is a plus. - Preferably based in Austin, TX (remote considered). What we offer 🎖️ A close-knit and collaborative early-stage startup environment where every voice is heard and every opinion matters 💰 Competitive salary and stock option equity packages 🏥 4 Medical Plans to choose from including 100% covered option. Plus Dental and Vision Insurance! 🤓 Learning & Growth stipend 🏠 Flexible long-term work options (remote and hybrid) 🥨 Free lunch provided in the office in NYC & Austin - you’ll never go hungry with us! 🛫 Unlimited PTO; We truly believe in work-life balance and that hard work should be balanced with time for rest and rejuvenation 🏝 IRL / In-Person retreats throughout the year Please note: All official communication from Trunk Tools will come from an email address ending in @trunk.tools. If you receive outreach from any other domain, please disregard it or report it to us. At Trunk Tools, we’re working hard to build a more productive and safer environment within the construction industry, and we strive to live by these same values here at Trunk Tools HQ. As an equal-opportunity employer, we are committed to building an inclusive environment where you can be you. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, or any other legally protected class.

• Own the end-to-end revenue operating model across Sales, Marketing, and Fulfillment • Lead annual and quarterly planning processes, including quota setting, territory design, and capacity planning • Translate company growth objectives into actionable GTM strategies and operational plans • Serve as the primary link between Finance and GTM, ensuring alignment between revenue forecasts, financial plans, and business performance • Own global revenue forecasting processes and accuracy, providing clear visibility to executive leadership • Define and manage pipeline coverage models, funnel metrics, and conversion benchmarks • Establish operating cadence including forecast calls, pipeline reviews, and quarterly business reviews • Deliver data-driven insights to inform executive decision-making and resource allocation • Design and scale processes across the full customer lifecycle (lead → opportunity → close → expansion → renewal) • Optimize lead management, routing, and conversion across Marketing and Sales Development • Identify and remove friction in the sales process to improve productivity, win rates, and cycle times • Standardize reporting and performance tracking across the GTM organization • Own the Revenue Operations technology stack (CRM, CPQ, marketing automation, and analytics tools) • Ensure data integrity, governance, and consistency across systems • Lead system enhancements, integrations, and automation initiatives to support scale • Evaluate and implement new technologies, including AI-driven tools, to improve GTM efficiency • Partner closely with Sales, Marketing, Customer Success, Product, and Finance to align on GTM strategy and execution • Provide operational and market insights to influence product, pricing, and growth strategies • Ensure seamless handoffs and accountability across the customer lifecycle • Act as a trusted advisor to executive leadership on revenue performance and operational strategy • Build and lead a high-performing global Revenue Operations organization • Develop strong leaders and create a scalable team structure aligned to business growth • Establish a culture of accountability, continuous improvement, and data-driven decision-making • Mentor and develop future leaders across the GTM organization

• Develop and maintain sales and marketing plans, along with an opportunity pipeline. • Sustain a high level of weekly sales activity. • Quickly evaluate opportunities and key strategic positions for each new prospect. • Establish and cultivate relationships at the executive, operational, and IT levels, with strong knowledge of our Products & Services in the B2B eCommerce market.

• Develop and implement a comprehensive enablement strategy tailored to Boulevard’s Customer Support organization. • Build onboarding, certification, and continuous learning programs that reduce time-to-productivity and improve resolution quality using Articulate and Workramp enablement tools. • Align enablement initiatives with CSAT, retention, resolution time, and operational efficiency goals. • Partner with Product and Engineering to integrate AI into customer communication workflows. • Train Support reps on effective AI usage and prompt best practices. • Continuously evaluate AI effectiveness using performance data and customer outcomes. • Build structured product education programs that deepen rep expertise. • Create ongoing release education processes to ensure Support stays ahead of product changes. • Develop certification programs to validate knowledge and skill development, as well as continued education and learning. • Partner with Product to translate complex functionality into clear, actionable guidance for frontline teams. • Ensure messaging consistency across channels (chat, email, phone). • Establish governance and quality standards for support content. • Create and maintain support playbooks, communication frameworks, troubleshooting guides, knowledge base enhancements, macro libraries, and ticketing workflows. • Use support performance data to identify skill gaps and improvement opportunities. • Use reporting frameworks and OKRs that connect enablement initiatives to measurable outcomes. • Partner with Support Leadership to continuously refine workflows and learning priorities. • Deliver engaging workshops, skill-based training sessions, and AI adoption programs. • Coach ICs and managers on reinforcing best practices, provide data and insight to leadership to help coach and direct ICS. • Create blended learning experiences (live, asynchronous, simulations, certifications).