Location: Boston, MA (Hybrid 3 days/week in Office)
Department: Customer Success
Reports To: VP of Global Revenue
Type: Full-time
Industry: M&A Software | B2B SaaS | Corporate Development
About Us
We’re a fast-growing B2B SaaS company transforming how Corporate Development teams manage M&A transactions. Our customer base includes leading acquirers and investment teams, and our software streamlines the complex, high-stakes M&A process from end to end.
Our Mission
Our mission is to create a world where M&A enables organizations and the ambitious people who build them, to achieve their full potential.
At DealRoom, we’re a community of forward thinking M&A practitioners on a mission to perfect the M&A process. We support teams with the unique combination of an open community, comprehensive educational resources, and innovative software products that help you navigate the modern day complexities of M&A transactions with confidence.
Our Values
Our culture is the heart of our success and our values guide everything we do at DealRoom.
Deliver the WOW
- Own the MVW: To balance speed and quality, we deeply understand our stakeholders, declare the MVW, deliver, and iterate - asap.
- Growth mindset: We embrace change, failure, AI, and continuous learning, so we can improve, innovate, and grow the business and ourselves.
- Enjoy the journey: Building is hard, and we believe that is why it’s so rewarding. We make it fun by celebrating wins, big and small.
Be Kind and Direct
- Care deeply: We lead with empathy, assume positive intent, and use the golden rule. And we believe that gossip is not kind or direct.
- Go direct: We never avoid the uncomfortable stuff. We get the right people together and embrace Radical Candor when we collaborate, debate, and IDS.
- Communicate thoughtfully: We communicate clearly, concisely, and timely to ensure we’re always on the same page. And we actively and vocally disagree-and-commit.
Own It
- In it to win it: We don’t punch a clock - we push ourselves, and our teammates, to compete and win. And we prioritize rest and wellness so we can win the marathon.
- Drivers wanted: We’re not interested in going along for the ride, we are all here to drive the bus. And we don’t just spot problems, we solve them.
- We before me: We always do what’s best for the greater good of our customers and the company. Including being frugal (not cheap).
The Role
We are hiring a
Head of Customer Success & Account Management to lead the entire post-sales organization, including:
- New customer onboarding
- The support function (AI-first strategy)
- All post-sales commercial ownership (renewals & expansion)
This leader will transform Customer Success into a modern, commercially accountable, and operationally efficient organization aligned to our bootstrapped model.
Responsibilities
Build & Develop a High-Performance CS Organization
- Recruit, hire, onboard, and develop top-tier CSMs, Account Managers, and Support professionals
- Establish the “Right People in the Right Seats”, performance metrics, and accountability frameworks to ensure we are delivering the wow for both prospective and current customers
- Create a culture of continuous coaching, mentoring, and performance improvement
- Build internal bench for future talent
Own and Optimize Post-Sales Commercials
- Develop and implement structured renewal and expansion playbooks
- Track, manage, and forecast all renewal and upsell opportunities with rigor
- Continuously optimize commercial processes to increase GRR and NDR
- Establish clear expansion strategy across segmentation tiers
- Introduce executive alignment motion in strategic accounts
- Ensure predictable renewal forecasting and risk management
Lead an AI-First Support & Onboarding Strategy
- Redesign onboarding to accelerate time-to-value
- Implement AI-first support motions aligned to our bootstrapped model
- Leverage modern CS tools, automation, and GTM engineering to increase:
- Efficiency
- Productivity
- Adoption
- Usage
- Value realization
- Build scalable, repeatable playbooks across the customer lifecycle
- Improve CSAT through structured feedback loops and proactive engagement
Optimize the existing infrastructure to increase retention and expansion (the now)
- Modernize Customer Success to proactively drive value realization
- Elevate the experience from reactive support to strategic partnership
- Establish clear health scoring and early risk detection
- Continuously iterate on tools, tech stack, and playbooks
Act as the Voice of the Customer (the future)
- Establish a strong partnership with Product
- Build structured VOC feedback loops
- Translate customer insights into product influence
- Diagnose and report on reasons for customer churn, creating actionable insights
- Inform roadmap priorities through data, trends, and customer patterns
Qualifications
- 7+ years in B2B SaaS Customer Success / Account Management
- Experience owning NDR/GRR within a meaningful revenue base
- Demonstrated success managing renewals and expansion targets
- Experience implementing scalable support and onboarding systems utilizing AI
- Fluency and comfort in analyzing customer segmentation/tiering to optimize headcount and book of business load as we scale
- Proven ability to build and develop teams
- Commercial operator with revenue forecasting rigor
- Strong analytical skills with deep CRM and CS platform fluency
- Proactive operator who leverages AI and automation
- Experience building playbooks and modern CS operating models
- Ability to balance strategic thinking with hands-on execution
- Executive presence and strong cross-functional partnership skills
Preferred Experience
- Experience operating within a bootstrapped, capital-efficient environment
- Strong partnership with Product organizations
- Track record of building VOC programs
- Experience owning pre-sales/sales engineering, as well as onboarding
Why Join Us?
- Opportunity to shape the entire post-sales engine
- Significant ownership and visibility
- Profitable, disciplined growth company
- Strong product-market fit with expansion opportunity
- Work closely with M&A leaders and elite Corporate Development teams
- Build a durable, modern CS organization from a position of strength
Benefits And Perks
- Wellness: PTO, 100% company paid medical, dental, and vision insurance, FSA options, as well as 401k + matching for our employees
- Invested in your future: Eligible employees enjoy new hire equity and a quarterly bonus structure tied to NDR/GRR performance
- Continuous learning: Curiosity is encouraged and supported
- Feedback culture: Radical candor and performance coaching are core
- International: Collaboration across cross-country teams
- Inclusive: We celebrate diversity across race, gender, age, orientation, religion, disability, and background
