Director of Sales

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’re looking for a Director of Sales to manage, grow, and further develop our sales team. In this role, you’ll work with sales team to drive sales strategy while owning the full sales lifecycle across all segments of our business. As a successful Director of Sales you have outstanding communication, negotiation, leadership, and influencing skills, and can seamlessly build a strong rapport with internal and external stakeholders. You have prior enterprise SaaS sales experience, the ability to maintain C-level relationships, work with a large extended team, and seven-figure deal experience. If you’re interested in helping shape the vision of Sales at Trunk Tools— apply today.

This role will report into our Vice President of Sales.

What you’ll do:

• Lead Trunk Tools’ Sales team to drive sales and achieves strategic objectives and quotas while fostering a culture of inclusion, accountability, and collaboration
• Support the development of Sales team through internal training and learning and development opportunities
• Manage your territory including planning, forecasting, and execution
• Contribute to and drive the GTM strategy
• Identify, engage, and qualify prospects; monitor progress through the sales cycle
• Establish and nurture relationships with key accounts to generate new business and expand revenue with current customers
• Sell to C-suite, solution sales, ability to sell to multiple stakeholders, selling against P/L, negotiating, presenting, closing
• Ensure a formal account engagement plan is developed and continually reviewed
• Work closely with Operations to continually develop tools to aid team to goal
• Structure and negotiate business terms and contracts with line-of-business, procurement, senior management and C-level executives
• Identify product improvements or new products by remaining current on customer needs, industry trends, market activities, and competitors
• Travel (25% - 50%)
  
  

What we’re looking for:

• 7-8+ years of software sales experience; proven experience identifying and closing seven figure contracts
• 3+ years of management experience in a sales environment (ideally SaaS)
• Experience in a sales leadership role with ability to increase sales through the development of high-performance teams and effective sales processes
• Demonstrated experience executing sales leadership methodologies and ownership of all aspects of territory management
• Extensive knowledge of enterprise SaaS models, SaaS metrics, and online sales models
• Ability to thrive in an entrepreneurial environment
• Experience selling licenses or subscriptions to large, complex organizations; experience selling into construction industry
• Construction experience (in any capacity) is a requirement
• A perfect mix of curiosity, empathy and ambition, resilience and optimism, competitive and value added mindset
  
  

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

3 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.

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Compensation Range: $160K - $300K