Senior Director of Global Sales Strategy and Operations, Ironclad
$225-280k
OTE
+ equity + bonus
2+ days a week in office
Enterprise software for managing contracts
Be an early applicant
Enterprise software for managing contracts
501-1000 employees
Be an early applicant
$225-280k
OTE
+ equity + bonus
2+ days a week in office
501-1000 employees
Company mission
To power the world’s contracts.
Role
Who you are
- 12+ years of progressive experience in Sales Operations, Revenue Operations, or GTM Strategy at a high-growth SaaS company
- 8+ years of people leadership, including experience managing managers, with a track record of building and developing high-performing ops teams
- Genuine AI fluency: you understand how AI tools work in a GTM context, evaluate use cases critically, and drive adoption with conviction, both inside the revenue org and in how the org sells externally. You don’t need to build agents. You need to speak the language and evaluate the ROI
- Proven experience leading multi-functional operations portfolios spanning sales ops, renewals, and partnerships, or equivalent scope, globally rather than in a single region
- A GTM-first mindset, with experience partnering across Sales, Marketing, Customer Experience, and Finance instead of optimizing for Sales alone
- Strong analytical skills: able to build forecasting models, work with complex datasets, and translate data into executive-ready narratives
- Deep familiarity with SaaS business mechanics: ARR, GRR, NDR, quota design, and partner economics
- Hands-on experience with the full GTM stack, including CRM, revenue intelligence platforms (forecasting, sales engagement, conversation intelligence, etc.), and AI productivity tooling (e.g., Claude, Actively, Glean, Minoa)
- A trusted, credible voice with sales leadership who can challenge assumptions and push back constructively while keeping the relationship strong
- Executive presence: equally effective presenting to front-line managers and C-suite audiences
- High ownership, low ego, bias toward action
What the job involves
- Ironclad is looking for a Sr. Director, Global Sales Strategy and Operations to own the operating infrastructure of the global sales organization: sales planning, pipeline and bookings performance, renewal and expansion execution, partner operations, and business development operations. This is a GTM-first role. You’ll partner as closely with Marketing, Customer Experience, Finance, and the GTM Engineering & Systems team as you do with Sales leadership, because we don’t win by optimizing one function alone
- This is also a data-first, AI-forward role. You’ll shape how Ironclad’s revenue org uses AI internally, in tooling and forecasting, and how our GTM motion adapts as buyers get more AI-savvy themselves. Bring firsthand experience with what AI can already do inside a revenue org, plus a point of view on what’s next
- This is not a ‘keep the lights on’ operations role. You will be responsible for automating away friction in our sales process, moving our team away from repetitive, transactional work and toward the strategic insights that actually move the needle
- This role calls for someone who will challenge sales leadership when the data calls for it: pressure-test plans, flag risk early, push back with evidence, and keep the relationship strong while doing it. This is a role for someone who wants to reshape how the business runs
- GTM Planning & Strategy
- Drive annual and long-range planning for the sales org, including new business, renewals, expansion, partners, and BDR, in partnership with Sales leadership and Finance
- Own territory design, quota allocation, compensation plan design, and capacity modeling for AE, CAE, BDR, and partner teams
- Define and maintain operating rules of engagement across GTM roles, so ownership, handoffs, and coverage stay clear as the business and its markets evolve
- Build the operational foundation for Ironclad’s international expansion, adapting planning frameworks, territory models, and cadences so global teams execute with the same rigor as the core business
- Revenue Intelligence & Accountability
- Simplify and automate our forecasting and pipeline reporting. Your goal is to give leadership one clean, central view of the funnel, freeing up everyone’s time to focus on closing deals rather than managing spreadsheets
- Drive accountability to the metrics that matter most: pipeline generation and coverage, net ARR and bookings attainment, and GRR and NDR performance, so the org closes gaps before they turn into missed targets
- Curate and lead our operating cadences—forecast reviews, deal inspections, and pipeline councils—ensuring they serve as a platform for real strategic decision-making, not just status updates
- In partnership with BI and Revenue leadership, define what gets measured and surfaced, then use that data to improve how the revenue organization operates and performs
- Sales Performance & Revenue Impact
- Turn trends across the funnel into programs that move the needle: a defined, forecastable expansion motion for the account management team, and renewal operations that deliver consistent GRR and NDR
- Build performance programs for partner- and BDR-sourced pipeline, including conversion analysis and enablement feedback, that lift their contribution to bookings
- AI & Transformation Leadership
- Use AI to supercharge our sales motion. We don’t just want someone to manage tools; we want someone who looks at our current workflow and asks, ‘How can we automate this?’ to make our sellers more effective and our forecasting more accurate
- Co-develop Ironclad’s GTM AI strategy as the primary field-side partner to the GTM Engineering & Systems team, so AI investments map to real field needs, with adoption tracked against clear metrics
- Strategic Leadership & Cross-Functional Influence
- Build and lead a high-performing operations team that shapes the business, and serve as a senior thought partner to Sales, Finance, and GTM leadership, translating signals into clear decisions and pushing back when the data calls for it
- Present to executive leadership with confidence, turning complex operational narratives into clear, data-backed recommendations for the CRO, CEO, and CFO
- Team Structure
- This role reports into the VP, Revenue Operations and Enablement. It leads a global sales operations team covering the Americas, EMEA, and APAC regions, along with strategy, planning, and sales programs. Structure and titles will flex based on the candidate and ongoing transitions
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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