Director of Customer Success & Account Management

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