Director Engineering Jobs in Kentucky (NOW HIRING)

Ironclad is the leading AI contracting platform that transforms agreements into assets. Contracts move faster, insights surface instantly, and agents push work forward, all with you in control. Whether you’re buying or selling, Ironclad unifies the entire process on one intelligent platform, providing leaders with the visibility they need to stay one step ahead. That’s why the world’s most transformative organizations, from Rivian to the World Health Organization and the Associated Press, trust Ironclad to accelerate their business.

We’re consistently recognized as a leader in the industry: a Leader in the Forrester Wave and Gartner Magic Quadrant for Contract Lifecycle Management, a Fortune Great Place to Work, and one of Fast Company’s Most Innovative Workplaces. Ironclad has also been named to Forbes’ AI 50 and Business Insider’s list of Companies to Bet Your Career On. We’re backed by leading investors including Accel, Y Combinator, Sequoia, BOND, and Franklin Templeton. For more information, visit www.ironcladapp.com or follow us on LinkedIn.

The Role

Ironclad is looking for a Director, GTM Engineering & Systems Architecture to build the agentic systems that will run our revenue organization. This is a hands‑on leadership role. You’ll lead a team of GTM engineers, systems architects, and CRM developers while also building out a team of autonomous agents. You will also personally design and ship the automation and AI agents that take over the manual work our Revenue teams do today.

You’ll be responsible for building out a world class revenue tech stack. The stack is already strong, but we need a leader with both experience and a deep vision for what the future of GTM tech looks like and a passion for driving us there. It’s a unique mix of managing vendor relationships, evaluating new tech, consolidating old tech, and building the connections between our data warehouse, CRM, and the autonomous systems that will run Ironclad’s revenue engine.

We’re adding one GTM Engineer to the team this year, and that’s likely it for a while. The goal is getting more out of agents than out of additional hires. This role owns how Ironclad scales GTM operations globally through automation and AI.

What You’ll Own

Agentic Systems & Automation

• Design and deploy autonomous agents to automate GTM workflows across Revenue, taking them from prototype to production systems the business relies on daily.
• Own how agents connect to the CRM, the data warehouse, and the rest of the revenue stack, including what data they can see and what actions they’re allowed to take.
• Implement essential guardrails, ranging from human-in-the-loop reviews for critical decisions to transparent permissioning, ensuring the team understands and trusts the agents' actions.
• Stay ahead of where agentic AI is going, and turn that into what Ironclad builds next.

GTM Tech Stack

• Set a multi-year vision roadmap for the tools that run the Revenue org, from forecasting and conversation intelligence to outbound engagement and the rest of the stack.
• Keep a close eye on the evolving tech landscape, evaluating consolidation opportunities and identifying when legacy tech becomes obsolete.
• Measure the adoption and impact of existing tech, partnering with the enablement team to ensure technology is being fully leveraged. And get the most out of existing tech before exploring further investments.

CRM & CPQ Platform

• Own Ironclad’s CRM architecture, including CPQ and how it connects to the rest of the revenue stack.
• Understand the voice and needs of the end users, staying close to field teams to ensure the system is meeting their needs.
• Constantly stay on the search for ways to simplify and automate elements of the deal cycle, reducing the demand for manual and time consuming data entry.

Team & Technical Leadership

• Set a technical bar high enough that you could personally build most of what you’d ask someone else to build.

Team Structure

This role reports to the VP, Revenue Operations & Enablement. It leads GTM engineering, systems architects, and CRM/CPQ administration functions. We’re adding one GTM Engineer this year. Autonomous agent development is a core initiative this role owns directly.

What You Bring

• 8+ years of hands‑on experience building AI systems and managing GTM tech stacks.
• A proven track record shipping production AI agents or LLM‑powered systems. Comfortable with agent frameworks and building with current models.
• Experience leading CRM and CPQ platform teams, including architecture, data model, and governance, at a company with GTM complexity.
• A genuine builder. You’re comfortable writing code and shipping systems yourself, not just directing engineers who do.
• Experience partnering with Revenue and Finance stakeholders, translating GTM needs into systems people actually adopt.
• You have a high‑ownership mindset and a low ego. You are comfortable running a team with a big, ambitious mandate.

OTE Range: $184,000-$230,000

+bonus +equity

The OTE range represents the minimum and maximum of the OTE range for this position based at our San Francisco headquarters. The OTE offered for this position will depend on numerous factors, including individual proficiency, anticipated performance, and the location of the selected candidate. Our OTE is just one component of Ironclad’s competitive total rewards package, which also includes equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure), competitive health and wellness benefits, and a commitment to career growth and development.

US Full-Time Employee Benefits at Ironclad:

• 100% health coverage for employees (medical, dental, and vision), and 75% coverage for dependents with buy‑up plan options available
• Market‑leading leave policies, including gender‑neutral parental leave and compassionate leave
• Family forming support through Maven for you and your partner
• Paid time off - take the time you need, when you need it
• Monthly stipends for wellbeing, hybrid work, and (if applicable) cell phone use
• Mental health support through Modern Health, including therapy, coaching, and digital tools
• Pre‑tax commuter benefits (US Employees)
• 401(k) plan with Fidelity with employer match (US Employees)
• Regular team events to connect, recharge, and have fun
• And most importantly: the opportunity to help build the company you want to work at

**UK Employee‑specific benefits are included on our UK job postings**

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.