Director of Enterprise Sales, CaptivateIQ
$350-400k
OTE
3 days a week in office
Commission management platform
Open for applications
Commission management platform
201-500 employees
Open for applications
$350-400k
OTE
3 days a week in office
201-500 employees
Company mission
To bring joy and transparency to sales performance management.
Role
Who you are
- Enterprise Sales Leadership: 8+ years of experience leading high-performing teams that sell complex, multi-stakeholder SaaS solutions to Finance, Revenue Operations, and IT at Fortune 1000 organizations
- Strategic Sales Experience: 5–8 years of proven success in B2B SaaS Enterprise closing roles; demonstrated expertise in managing six-figure deal cycles involving complex stakeholder groups, formal RFPs, and rigorous Procurement/IT evaluations (preferably with technical or financial products)
- Operational Rigor: Expert-level command of disciplined, metrics-driven sales engines; highly proficient in pipeline creation, qualification methodologies (e.g., MEDDIC), forecast hygiene, and coaching AEs through "enterprise-class" execution
- Scaling & Team Building: Proven track record of scaling an enterprise segment, including defining territory/coverage models and a demonstrated ability to recruit, onboard, and develop top-tier Enterprise Account Executives
- Domain & Market Expertise: Deep understanding of the ICM/SPM landscape, RevTech, or adjacent financial systems; ability to credibly position a modern solution against legacy platforms (e.g., Xactly, Varicent) or complex manual processes
- Value-Based Selling: Highly fluent in ROI-based selling and business case development, focusing on operational efficiency, risk/compliance, and the strategic revenue impact of incentive compensation
- Technical & Security Literacy: Strong grasp of enterprise-grade requirements including security/compliance (SOC, SOX), governance, third-party integrations, and complex change management
- Executive Presence & Influence: Exceptional ability to partner with C-level stakeholders externally and influence internal Product and Engineering leaders to align roadmaps with enterprise market needs
- Ecosystem Strategy: Prior experience leveraging Global Systems Integrators (GSIs), referral partners, and broader software ecosystems to accelerate deal cycles and expand market reach
What the job involves
- As our Director of Enterprise Sales, you will own CaptivateIQ’s enterprise new business motion, with a mandate to drive predictable ARR growth across our largest and most strategic accounts
- You will be responsible for setting the enterprise go-to-market strategy, building territory and account plans, and ensuring our teams remain deeply aligned with customers’ sales performance priorities
- In this role, you will define and uphold a high-caliber sales process—from multi-threaded discovery through value-based validation and executive alignment—while maintaining rigorous pipeline and forecasting cadences
- Reporting directly to the VP of Sales, you will be a visible partner to senior leadership on how we win and expand in the enterprise segment
- You will lead a high-performing team of Enterprise Account Executives focused on landing and expanding CaptivateIQ within complex, multi-stakeholder organizations
- You will be accountable for scaling the team through hiring, onboarding, and continuous development, while fostering a culture of accountability and coaching
- Strategic Deal Coaching: Actively participate in high-stakes customer meetings, providing "player-coach" support to navigate complex procurement, legal, and executive-level negotiations
- Pipeline & Forecast Accuracy: Maintain a rigorous cadence of deal reviews and pipeline inspections to ensure forecast predictability and high-velocity stage progression
- Revenue Growth: Accountable for meeting or exceeding quarterly and annual ARR targets for the Enterprise segment through new logo acquisition and strategic expansion
- Solution Design & ROI: Partner with Solutions Engineering and Value Consulting to architect enterprise-grade demonstrations and business cases that quantify ROI and prove the platform's ability to solve complex incentive compensation challenges
- Operational Excellence: Collaborate with Revenue Operations to optimize territory design, quota setting, and coverage models, ensuring internal sales processes mirror the industry best practices recommended to clients
- GTM & Ecosystem Alignment: Coordinate with Marketing and Partnerships to execute high-touch Account-Based Marketing (ABM) campaigns and leverage ecosystem partners to displace legacy ICM/SPM incumbents
- Customer Lifecycle Management: Oversee the transition from sales to Customer Success and Professional Services to ensure seamless, low-risk implementations and to strategically identify expansion opportunities within existing accounts
- Product Influence & Feedback Loop: Serve as the "voice of the enterprise" for Product and Engineering, translating field requirements—specifically regarding security, compliance (SOC/SOX), and advanced integrations—into actionable roadmap priorities
Our take
CaptivateIQ is an incentive compensation platform using AI to automate commission workflows. Businesses spent an exorbitant amount each year managing commission processes, so the company's no-code SaaS is a welcome overhaul for the sector.
CaptivateIQ's platform improves both the efficiency and accuracy of existing legacy processes, serving any type of organization that utilizes a performance-based compensation plan. The founding team has real experience with the cumbersome process of managing commission payments, which is why they chose to target this particular problem.
CaptivateIQ has been smart in building a more generic product, allowing it to attract big-name clients from different sectors. This broad customer acquisition, atop regular funding injections, has helped CaptivateIQ reach Unicorn status. The company continues to add to its offering, for example with the launch of its AI-powered payee experience in 2025.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-14% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Jan 2022
$100m
SERIES C
Apr 2021
$46m
SERIES B
Total funding: $159.2m
Company benefits
- 100% of medical, dental, and vision covered including 75% for dependents 🇺🇸
- Unlimited vacation days and quarterly mental health days so you can recharge 🇺🇸
- $1,000 to explore your dream destination on your work anniversary 🇺🇸
- $500 annual professional development stipend to continue growing and learning 🇺🇸
- $500 home office stipend to decorate your home office 🇺🇸
- $1,000 caretaker stipend to make sure our parent colleagues are being supported 🇺🇸
- Virtual team lunches to keep you connected 🇺🇸
- 401k plan to participate in and save towards the future 🇺🇸
- Newest hardware and tools for the job 🇺🇸
- Employee Resource Groups (ERGs) to support and celebrate the shared identities and life experiences of communities within CaptivateIQ 🇺🇸
Company HQ
China Basin, San Francisco, CA
Leadership
Mark Schopmeyer
(Co-CEO & Co-founder)Former Investment Professional at Carrick Capital Partners and Finance and Strategy Manager at BrightRoll. Former Investment Banking Analyst at Jefferies & Company and Lehman Brothers. BA in Business Administration from Berkley School of Business.
Conway Teng
(Co-CEO & Co-founder)Former employee at Gusto in Finance and Business Operations. Previously Head of Growth at OrderAhead. Founder of FiveStars. Graduated from Berkley.
Hubert Wong
(Principal Engineer & Co-founder)Was CTO of the company for 6 years. Former Senior Software Engineer at Vungle, OpenTable and CoPilot Labs. BS in Electrical Engineering and Computer Science at Berkley.
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