Dennis K. Hennessey

Founder

Boston, MA, United States23 yrs 10 mos experience

Key Highlights

  • Over 20 years in Customer Success and Operations.
  • Achieved 100% client retention across multiple roles.
  • Expert in transforming operational processes for scalability.
Stackforce AI infers this person is a Customer Success Operations Leader in the SaaS industry.

Contact

Skills

Core Skills

Operations ManagementCustomer Experience ManagementAccount ManagementCustomer SuccessBusiness Development

Other Skills

Start-up LeadershipCoachingCustomer RetentionBusiness Process ImprovementProcess ImprovementCross-functional Team LeadershipChannel PartnershipsSales OperationsConsultingValue PropositionsUpsellingCross-functional CollaborationsRelationship BuildingChange ManagementProject Management

About

I believe that a CS team is only as strong as the operations powering it. With over 20 years of experience in Account Management, Customer Success, and Operational Transformation, I help organizations move past manual hurdles and toward scalable, automated success. My mission is simple: ELIMINATE FRICTION, CODIFY BEST PRACTICES, AND USE DATA TO TELL THE STORY OF CUSTOMER SUCCESS. I bring a proven ability to build and grow high-value relationships while aligning operational strategy with business outcomes. I've led enterprise account portfolios, negotiated renewals and contract expansions, and partnered with cross-functional teams across product, operations, and executive leadership to drive measurable growth and retention. Throughout senior leadership roles including VP and Director positions, I have consistently developed strategic account programs, leading cross-functional initiatives, and translating performance data into actionable business strategy positions me well to manage and grow complex partnerships. I focus on creating consistency at scale by bridging the gap between Customer Success strategy and measurable financial outcomes. From streamlining global renewal workflows to building high-performing Ops teams, I am committed to turning customer health data into actionable growth strategies. By linking operational KPIs to NRR and profitability, I ENSURE THAT CUSTOMER SUCCESS ISN'T JUST A SERVICE, IT’S A PRIMARY DRIVER OF THE BOTTOM LINE. Leadership Philosophy: Over the years, I’ve learned that leadership has less to do with having the right answers and more to do with creating the right environment. After more than two decades working across Customer Success, Account Management, and Operations, what stands out most isn’t process — it’s people. I try to lead with empathy, curiosity, and steadiness. I’ve seen that when people feel heard and trusted, they bring better ideas, take greater ownership, and grow in confidence. My role is often to listen first, ask thoughtful questions, and provide clarity when it’s needed — not to dominate the room. I value direct, honest conversation, but I believe it can be delivered with respect and care. Accountability matters, but so does dignity. Especially in moments of pressure, I aim to be calm, fair, and consistent. If the people around me feel supported, challenged in healthy ways, and stronger than when we began working together, I consider that meaningful leadership. If my team becomes more confident and capable over time, that’s success to me.

Experience

Ferryway consulting partners

Founder

Sep 2025Present · 7 mos · New Hampshire, United States · Remote

  • Specializing in customer experience design, process optimization, and journey mapping - helping leaders streamline operations, uncover efficiencies, and build scalable business models.
Operations ManagementStart-up LeadershipCoachingCustomer Experience Management

Healthaxis group

VP, Account Management and Commercial Strategy

Feb 2025Oct 2025 · 8 mos · Remote

  • Driving growth and nurturing client relationships through Strategic Account Management, Channel Partnerships, and Sales Operations.
  • Transformed operational Account Management leading to budget reduction and no red clients.
  • Achieved a 100% increase in referenceable customer accounts.
  • Directed renewal and recontracting initiatives, contract longevity, and doubling contract profitability.
  • Collaborated with sales leaders to refine deal strategies, enhancing execution through improved messaging, content, meetings, pricing, and contracting.
  • Established and managed a Channel Partner program, cultivating essential reseller relationships and developing Go-To-Market Plans to grow sales pipeline.
  • Directed Account and Sales Operations by implementing effective processes, tools, and methodologies, restructuring the Strategic Account Management resource model for improved efficiency and scalability
Operations ManagementCustomer Experience ManagementCustomer RetentionBusiness Process ImprovementProcess ImprovementCross-functional Team Leadership+2

Healthedge

Executive Customer Partner

Jan 2024Jan 2025 · 1 yr · Burlington, Massachusetts, United States · Remote

  • Cultivated operational and executive alliances to drive strategic account initiatives, value realization, and and product adoption.
  • Achieved a 100% CLIENT RETENTION RATE
  • Fostered organizational adoption by delivering tailored strategic consulting services.
  • Provided revenue-generating solutions, data analytics and training, to effectively meet client needs.
ConsultingValue PropositionsAccount ManagementUpsellingCross-functional CollaborationsRelationship Building+1

Healthaxis group

Vice President, Operational Enablement

May 2022Dec 2023 · 1 yr 7 mos · Tampa, Florida, United States · Remote

  • Responsible for working with cross-functional leaders throughout the company to support long-term strategies that drove operational efficiencies and increased productivity, while materially impacting the overall customer experience. Advocated, drove, and implemented internal solutions, projects, strategies, methodologies, processes, training, and other actions to better support our customer impacting teams.
  • Direct ownership of the Internal Project Management and Training Services departments.
  • Improved operational efficiency by streamlining staff roles and eliminating redundant processes.
  • Identified 60 improvement areas through performance metrics analysis and business tools to boost productivity.
  • Developed and implemented an Account Management training program, restructuring roles for strategic engagement, leading to a 30% increase in referenceable customers.
  • Led teams in Training Services and Internal Project Management to optimize processes, resulting in a $1 million revenue increase from overhauling the Change Request Process.
Business Process ImprovementProject ManagementCustomer Relationship Management (CRM)Customer SuccessOperations ManagementCustomer insights

Edcast

Director of Customer Success (North America)

Jul 2021May 2022 · 10 mos · Remote

  • Led a team of CSMs with a responsibility to ensure our customers realized the full value of our products and services. Drove forward Customer Success best practices and processes.
  • Directed a team of Customer Success Managers, enhancing client relationships and elevating CSAT.
  • Developed Standard Operating Procedures that increased departmental efficiency and productivity.
  • Implemented a scalable Account Management model to support notable business expansion.
  • Led the global roll out of our CRM, Gainsight
Account ManagementLeadershipCross-functional CoordinationTeam BuildingRenewalsCustomer Satisfaction+2

Healthedge

Sr. Director of Customer Success Operations

Oct 2018Jun 2021 · 2 yrs 8 mos · Burlington, Massachusetts, United States · Remote

  • Established account management best practices by designing, creating and implementing new programs, tools, and processes to support and enable Account Management teams across 3 business units. Partnered with Sales, Professional Services and Marketing to develop and deliver a scalable, streamlined, and predictable experience that delighted our customers and drove exponential account growth.
  • Executed strategic initiatives to enhance customer satisfaction and operational efficiency
  • Led cross-functional teams to optimize processes and improve service delivery, contributing to business growth through a focus on Customer Success metrics.
  • Developed and executed Account Management processes, resulting in a 50% increase in Net Promoter Score and the establishment of a customer reference program within 48 activities.
  • Managed tool enablement projects, including a comprehensive Salesforce rebuild and the implementation of Coveo search and Confluence enhancements, contributing to ServiceNow project development.
  • Transformed support model to proactive engagement, achieving 120% growth in the value-added funnel and creating customer health scoring, KPIs, and an opportunity tracking process for improved experience scalability and predictability.
Cross-functional CollaborationsOperations ManagementProject ManagementCustomer InsightCustomer Satisfaction (CSAT)Customer Retention+4

Welltok, inc.

Sr. Director of Engagement Management

Jul 2016Oct 2018 · 2 yrs 3 mos · Burlington, MA · Remote

  • Led a team of Engagement Managers who were wholly passionate about nurturing client relationships, enhancing member experiences, and ensuring customers were realizing the full value of Welltok's robust offering of solutions. 100% CLIENT RETENTION RATE.
  • Led a team to exceed performance targets, enhancing overall business outcomes.
  • Maintained client relationships with a 100% retention rate, preserving $35 million in revenue.
  • Implemented a strategic management approach that achieved the highest organizational Net Promoter Score (NPS) and consistent revenue growth.
  • Led a team to enhance client engagement strategies by integrating customer feedback into service improvements, resulting in strengthened partnerships.
  • Analyzed market trends and customer needs, contributing to product development initiatives and reinforcing a commitment to client-driven innovation.
Account ManagementRenewalsBusiness Process ImprovementCustomer SatisfactionLeadershipGlobal Cross-Functional Team Leadership+1

Signiant

Director of Customer Success

Jun 2015Jul 2016 · 1 yr 1 mo · Lexington, Massachusetts

  • Developed and launched the Customer Success program. Established, implemented and fine tuned a multitude of processes designed to increase adoption, growth, retention rates, and enhance the customer's overall experience.
  • Developed a Customer Success Management program focused on leadership and strategic initiatives, which improved client retention by 100% and satisfaction by 50%.
  • Established and led day to day Account Management SOPs and C-Level reporting.
  • Conducted monthly training webinars and created a churn risk assessment tool, enhancing customer engagement and reducing churn rates.

Wtd consulting

Customer Success/Experience Consultant

Aug 2014Jan 2024 · 9 yrs 5 mos · Greater Boston Area · Remote

  • Guided Customer Success leaders in developing scalable processes and tools. Established methodologies aimed at achieving customer satisfaction targets.
ConsultingChange ManagementProject ManagementCustomer ExperienceOperations ManagementCustomer Success+1

Nasuni

Customer Success Manager, Sr.

Dec 2012Jun 2015 · 2 yrs 6 mos · Natick, MA

  • Launched the Customer Success program. Established and implemented a number of internal and external processes that led to a more efficient workflow within our PS organization and optimized the customer experience, leading to EXPONENTIAL growth. Oversaw an extensive account list that included our highest revenue generating accounts while continuing to cultivate Nasuni's Customer Success Program. *100% CLIENT RETENTION RATE*

Varolii

3 roles

Customer Success Manager

Jun 2011Dec 2012 · 1 yr 6 mos

  • Launched and defined the Customer Success Manager position. Established a management system and processes, which received executive approval that were adopted as our baseline Customer Success program. By adopting these processes, my team and I restored balance to struggling accounts, which led to exceeding of our annual sales goals. *100% CLIENT RETENTION RATE*

Technical Account Manager

Sep 2010Jun 2011 · 9 mos

  • Primary point of contact between major strategic accounts and Varolii’s cross-functional teams including Sales, Product Management, Support, and Product Marketing. Directed the ongoing customer management process. *100% CLIENT RETENTION RATE*
  • Additionally, I supported Account Executives as a technical specialist with new direct prospects and new growth opportunities within our install base.

Partner Advocate, Sr.

Dec 2008Sep 2010 · 1 yr 9 mos

  • Defined, launched, and continuously developed the Partner Advocate program. Conceived and implemented corrective processes and operating procedures that ensured attentive, dependable service across our Professional Services and Engineering teams. Oversaw all of our partner relationships and protected 80% of our total revenue. *100% CLIENT RETENTION RATE*
  • Other responsibilities included, managing the Application Engineering team’s work queue, project managed Professional Services work as it related to the partners, and prioritized and drove new product enhancement requests.

Iron mountain

Technical Account Manager

Apr 2008Dec 2008 · 8 mos

  • As the first Technical Account Manager at Iron Mountain Digital, I established an account management standard that dramatically increased customer satisfaction levels throughout my client list, which was comprised of seven of Iron Mountain's top 10 customers. *100% CLIENT RETENTION RATE*
  • Additionally, I was responsible for the ongoing development of Iron Mountain's Technical Account Manager Program and served as a liaison between clients and Support, Engineering, Sales, and upper management.
  • (Left the company to follow my hiring manager to Varolii)

Wxrv, 92.5 the river

Director of New Media Development and Local Sales

Jan 2007Apr 2008 · 1 yr 3 mos

  • Developed and implemented New Media marketing initiatives. Responsibilities included maintaining and growing our top 2 revenue-generating clients while managing vendors and employees. Established budgets for website design and other projects.

Massachusetts army national guard

Specialist

Dec 1992Dec 1998 · 6 yrs · Melrose, MA

  • Drove an M113 armored personnel carrier for our mechanized infantry division.

Education

University of Denver

Master of Science - MS — Organizational Leadership w/ concentration in Organizational Operations

Sep 2028Present

Emerson College

Bachelor of Arts Degree — Communications

Stackforce found 100+ more professionals with Operations Management & Customer Experience Management

Explore similar profiles based on matching skills and experience