Senior People Operations Director, Ironclad
Systems & Data
$245-265k
+ Equity + Bonus
Enterprise software for managing contracts
Be an early applicant
Enterprise software for managing contracts
501-1000 employees
Be an early applicant
$245-265k
+ Equity + Bonus
501-1000 employees
Company mission
To power the world’s contracts.
Role
Who you are
- 10+ years of progressive leadership experience across People Operations, People Systems, HR Technology, Workforce Planning, Business Operations, or a related field in a high-growth environment
- 4+ years leading managers and building high-performing operational, systems, or analytics teams
- Deep experience with HRIS, payroll, planning, and adjacent enterprise systems, along with a strong understanding of how data should flow across them
- Strong analytical fluency, including experience designing reporting frameworks, identifying root causes, and translating data into executive-level decisions
- Proven success leading systems implementations, process redesign, or operating-model improvements that materially improved scale, quality, or speed
- Experience building strong cross-functional partnerships with Finance, IT, Talent Acquisition, and business leaders
- Demonstrated judgment in balancing service, rigor, speed, and change management in a dynamic environment
- A practical, hands-on orientation: you can move between strategic design, operational detail, and executive influence with ease
- Clear point of view on how AI and automation can improve People work, paired with discipline around governance, quality, and adoption
- Excellent communication skills, with the ability to bring clarity to ambiguity and align stakeholders around decisions
- A builder’s mindset, strong ownership instincts, and high standards for execution
What the job involves
- The People team at Ironclad is building the operating foundation that helps the company scale with clarity, speed, and high standards
- We care deeply about employee experience, and we also believe the next chapter requires stronger systems, sharper data, cleaner operating discipline, and more modern ways of working
- We're looking for a systems-driven leader to define and build People Operations, Systems, and Data as a true leadership capability at Ironclad — owning the infrastructure, workforce data, and operational rigor that will power the People team's next stage of scale
- You will serve as a strategic partner to the CPO and a cross-functional operator across Finance, IT, and G&A — simplifying fragmented processes, strengthening workforce data quality, and building the scalable operating model
- The ideal candidate brings strong operational leadership, deep systems and analytics fluency, and a practical point of view on how AI, automation, and better process design can materially improve employee experience and organizational effectiveness
- Lead the strategy, roadmap, and execution for People operations, systems, and data at Ironclad
- Own and modernize the core People infrastructure, including HR systems, workflows, data governance, and reporting foundations
- Partner with Finance, IT, and cross-functional operators to improve the architecture connecting headcount, org, payroll, recruiting, and planning data
- Build a more scalable operating model for People by simplifying processes, clarifying ownership, reducing manual work, and strengthening documentation and controls
- Drive workforce data quality and establish clear governance for core employee, organizational, and planning data
- Lead People analytics and executive reporting, translating complex data into clear insights, tradeoffs, and recommendations for business and People leaders
- Build planning rhythms and operating mechanisms that improve prioritization, execution, and follow-through across the People team
- Identify and operationalize high-value opportunities to use AI and automation across People workflows, with an emphasis on reliability, governance, and measurable business impact
- Serve as a strategic thought partner to the Chief People Officer and the People leadership team on organizational health, capacity, workforce planning, and operating effectiveness
- Hire, develop, and lead a high-performing team across People Operations, systems, analytics, and program execution
- Establish a culture of accountability, service orientation, experimentation, and continuous improvement
- Ensure operational excellence across core People processes, including compliance-sensitive workflows, audits, documentation standards, and change management
Our take
Business contracting is often inefficient and messy, with approvals required from various stakeholders and many processes still paper-based. Ironclad is a platform that digitises, automates, and streamlines contract workflows, allowing legal teams to focus on legal work rather than paperwork. Its platform features collaborative tools that facilitate business operations and extract and catalogue contract metadata, making information easier to access and act upon. Its enterprise customers include Dropbox, Mastercard, Pixar, Fox, and L’Oréal.
Despite its success, Ironclad faces competition in the $3.68 billion contract lifecycle management industry from major players like DocuSign and emerging ones like Contractbook. The company recently announced Ironclad Signature, marking its entry into the $13 billion eSignature market. The new feature speeds up the signature process by an estimated 80% and provides summaries and approval histories to users. This new tool is expected to strengthen Ironclad's position in the sell-side contract lifecycle management market.
Additionally, Ironclad introduced value-based pricing, charging only for completed, signed agreements, unlike other providers who charge for every signature packet sent out. Ironclad, backed by investors like Accel, Sequoia, Y Combinator, and BOND, remains committed to innovating and maintaining its leadership in the contract lifecycle management space.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
-3% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Jan 2022
$150m
SERIES E
Dec 2020
$100m
SERIES D
Total funding: $334.3m
Company benefits
- Dental, and vision insurance
- 401K
- Wellness reimbursement
- Flexible vacation policy
- Generous parental leave for both primary and secondary caregivers
- Work from home opportunities
- Health insurance
Company HQ
Chinatown, San Francisco, CA
Leadership
Cai GoGwilt
(Co-Founder & Board Member)Studied HSPS at Cambridge, and Computer Science at MIT. Was a Summer Technology Analayst at Goldman Sachs. Worked as a Research Assistant at MIT. Was a Software Engineer at Palantir.
Jason Boehmig
(Co-Founder & Board Member)Former Corporate Lawyer at Fenwick and Professor of Law at the University of Notre Dame before founding Ironclad in 2014.
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