What are the responsibilities and job description for the Director of AI Transformation position at Qumis?
About Qumis
Qumis is an expert AI built for the top minds in insurance. Our attorney-trained AI delivers clarity, speed, and legal-grade reasoning for brokers, claims professionals, and risk managers handling the industry's most complex risks. Founded in 2023 and backed by world-class investors, we're transforming how insurance professionals analyze policies, compare coverage, and serve their clients.
Our culture: Move fast. Use AI. Be data-driven.
What Our Customers Say:
"Qumis is a revelation. It's the only tool I've seen that truly feels like it was built by and for insurance experts."
— Brian Pilarski, SVP & Partner, Kapnick Insurance
"It is like a first-year associate—only faster and more accurate."
— Tom Hanekamp, Senior Partner, Cruser Mitchell
The Role: Operationalize and Scale Our Success Engine
70% of AI implementations fail. Your job is to make sure Qumis customers are in the 30% that succeed.
You’ll be our first Customer Success hire, which means you’re not just a support contact, you’re a strategic partner who holds clients accountable to their own goals. Insurance professionals don't adopt AI because it's cool; they adopt it when it saves them 5 hours every Monday and helps them win placements they would have lost. Your job is to engineer that outcome, repeatedly, for dozens of customers.
This isn't a hand-holding role. It's a high-leverage position where you'll drive customer outcomes, own retention, and build the systems that scale our CS function to 100 customers. You'll work directly with insurance firms implementing AI into their daily workflows—a transformation that requires behavioral change, executive influence, and relentless focus on adoption metrics.
Key Responsibilities
Drive Revenue Through Customer Success (40% of role)
You Have:
Most CS roles are theater. You run QBRs that everyone knows are performative. You track CSAT scores that don't correlate with retention. You manage relationships but don't own outcomes. This role is different.
You'll own retention outcomes from day 1. Not "drive adoption and hope it leads to renewals." You'll build the renewal business case, run QBRs that prove ROI, and set the stage so that when your Sales partner steps in to close, it's a layup. Your success is tied to whether customers renew because your work determines whether that renewal is inevitable or a fight. You'll present directly to the C-suite throughout the customer lifecycle, building the credibility that makes the final conversation a formality. No hiding behind "I did my part, Sales lost the deal."
You'll build systems that outlive you. Most first CS hires inherit chaos and fight fires forever. You're coming in with a structured implementation framework, proven adoption metrics, and executive buy-in. Your job is to operationalize what works and systematize what you learn. In 18 months, when we hire CS Manager #5, they'll be using systems you built.
You'll work on the most important problem in tech. AI adoption is the defining challenge of the next decade. Most AI tools get tried once and abandoned. You'll figure out how to make AI stick—how to change 20-year industry veterans' behavior, how to prove ROI in 30 days, how to turn skeptics into champions. That's a resume-defining skillset.
You'll work with founders who get it. We built this implementation framework because we saw customers churn despite "successful" deployments. We know what really works. We've codified this into playbooks before hiring you, which means you're not starting from zero—you're scaling what works.
The timing is perfect. You're joining early enough to define the CS function but late enough that we have product-market fit, paying customers, and proven adoption playbooks. You won't spend 6 months "figuring out what customers need"—you'll spend 6 months scaling what already works.
Compensation Range: $150K - $180K
Qumis is an expert AI built for the top minds in insurance. Our attorney-trained AI delivers clarity, speed, and legal-grade reasoning for brokers, claims professionals, and risk managers handling the industry's most complex risks. Founded in 2023 and backed by world-class investors, we're transforming how insurance professionals analyze policies, compare coverage, and serve their clients.
Our culture: Move fast. Use AI. Be data-driven.
What Our Customers Say:
"Qumis is a revelation. It's the only tool I've seen that truly feels like it was built by and for insurance experts."
— Brian Pilarski, SVP & Partner, Kapnick Insurance
"It is like a first-year associate—only faster and more accurate."
— Tom Hanekamp, Senior Partner, Cruser Mitchell
The Role: Operationalize and Scale Our Success Engine
70% of AI implementations fail. Your job is to make sure Qumis customers are in the 30% that succeed.
You’ll be our first Customer Success hire, which means you’re not just a support contact, you’re a strategic partner who holds clients accountable to their own goals. Insurance professionals don't adopt AI because it's cool; they adopt it when it saves them 5 hours every Monday and helps them win placements they would have lost. Your job is to engineer that outcome, repeatedly, for dozens of customers.
This isn't a hand-holding role. It's a high-leverage position where you'll drive customer outcomes, own retention, and build the systems that scale our CS function to 100 customers. You'll work directly with insurance firms implementing AI into their daily workflows—a transformation that requires behavioral change, executive influence, and relentless focus on adoption metrics.
Key Responsibilities
Drive Revenue Through Customer Success (40% of role)
- Own renewal and expansion revenue targets for your portfolio
- Run executive QBRs that prove ROI, address risks early, and position expansion opportunities
- Build renewal business cases using usage data, time savings analysis, and business impact narratives
- Identify and drive expansion opportunities (new teams, new workflows, seat growth)
- Partner with Sales on at-risk renewals and upsell conversations
- Guide customers through structured 12-week implementations that achieve industry leading adoption and retention
- Navigate organizational change management—this is behavioral transformation, not software deployment
- Enforce accountability: You must be comfortable telling a client VP that their implementation is failing and what needs to change to fix it.
- Intervene rapidly when adoption stalls (you have 48 hours, not 48 days)
- Translate early warning signals in usage data into targeted interventions
- Create repeatable playbooks from implementation learnings (onboarding flows, training frameworks, health scoring)
- Build data dashboards that predict churn before customers know they're at risk
- Document common failure patterns and design interventions that prevent them
- Enable future hires to replicate your success through structured systems
- Share insights with Product on friction points and expansion opportunities
- Month 6: Achieve 90% gross retention rate across your portfolio and close your first expansion deal by proving ROI to executive stakeholders
- Month 12: Own $2M in ARR with 95% retention and 120% net revenue retention while scaling CS processes to support 30 active customers
You Have:
- 5-7 years in insurance, legal tech, or high-stakes professional services (former consultants welcome)
- You have experience serving clients where accuracy is non-negotiable (e.g., brokers, attorneys, auditors, or compliance officers)
- You can speak fluently about complex workflows and producer compensation
- You have credibility with 20-year industry veterans, not just tech-forward adopters
- Enterprise implementation experience managing complex, multi-stakeholder rollouts
- Led 5 implementations requiring executive sponsorship and organizational change
- Understand that successful deployment ≠ successful adoption
- Know how to diagnose why trained users aren't using the platform
- Data-driven decision-making as your default operating mode
- Build dashboards without being asked (and actually use them)
- Can explain the difference between leading indicators (weekly engagement patterns) and lagging indicators (NPS scores)
- Default to "let's look at the data" rather than "I think..."
- Executive influence skills (without org chart authority)
- Have run QBRs with VP stakeholders where you drove their decisions
- Comfortable telling a COO their implementation is failing and exactly what needs to change
- Can translate technical adoption metrics into business impact narratives
- Builder mentality for creating systems from scratch
- Have built customer success processes from zero (not just operated existing ones)
- Think "how do I scale this to 100 customers?" even when there are only 5
- Thrive in ambiguity—don't need perfect documentation before being productive
- Commercially oriented: You understand that your job is driving revenue retention, not just customer satisfaction
- Precision-oriented: You understand that Qumis provides legal-grade reasoning. You respect that hallucinations or errors in our world aren't just bugs—they are liabilities. You sweat the details because our customers do.
- Action-biased: You ship version 1 and iterate rather than planning for perfection
- AI-native: Already using Claude/ChatGPT daily and excited about AI transforming insurance
- Outcome-obsessed: Measure success by customer results (time saved, deals won), not activity (training sessions delivered)
- Comfortable with conflict: Will push back on executive stakeholders when their behavior risks implementation success
- Screening (30 min): Domain fluency change management experience
- Case Study (take-home 60 min presentation): Diagnose a failing implementation and build your intervention plan
- Executive Simulation (45 min): Role-play a QBR with a COO questioning a renewal
- Culture Fit (30 min): Meet founders and assess alignment with "move fast use AI be data-driven"
- Base Salary: $150,000 - $180,000 (based on experience)
- Equity: 0.15% - 0.25% early employee grant (4-year vest)
- Benefits: Health/dental/vision, unlimited PTO, $1,000 annual home office stipend
Most CS roles are theater. You run QBRs that everyone knows are performative. You track CSAT scores that don't correlate with retention. You manage relationships but don't own outcomes. This role is different.
You'll own retention outcomes from day 1. Not "drive adoption and hope it leads to renewals." You'll build the renewal business case, run QBRs that prove ROI, and set the stage so that when your Sales partner steps in to close, it's a layup. Your success is tied to whether customers renew because your work determines whether that renewal is inevitable or a fight. You'll present directly to the C-suite throughout the customer lifecycle, building the credibility that makes the final conversation a formality. No hiding behind "I did my part, Sales lost the deal."
You'll build systems that outlive you. Most first CS hires inherit chaos and fight fires forever. You're coming in with a structured implementation framework, proven adoption metrics, and executive buy-in. Your job is to operationalize what works and systematize what you learn. In 18 months, when we hire CS Manager #5, they'll be using systems you built.
You'll work on the most important problem in tech. AI adoption is the defining challenge of the next decade. Most AI tools get tried once and abandoned. You'll figure out how to make AI stick—how to change 20-year industry veterans' behavior, how to prove ROI in 30 days, how to turn skeptics into champions. That's a resume-defining skillset.
You'll work with founders who get it. We built this implementation framework because we saw customers churn despite "successful" deployments. We know what really works. We've codified this into playbooks before hiring you, which means you're not starting from zero—you're scaling what works.
The timing is perfect. You're joining early enough to define the CS function but late enough that we have product-market fit, paying customers, and proven adoption playbooks. You won't spend 6 months "figuring out what customers need"—you'll spend 6 months scaling what already works.
Compensation Range: $150K - $180K
Salary : $150,000 - $180,000