Todd Jacobsen

Todd Jacobsen

Customer Success & Post-Sale Leader | Head of CS | 25+ Years in Enterprise SaaS

25 yrs experience · Newbury, MA · <10 hrs/week

About

Customer Success & post-sale executive with 25+ years of progressive experience across enterprise SaaS and global technology platforms, specializing in building and leading disciplined, scalable customer success organizations. Known for transforming reactive, under-structured post-sale environments into high-performing CS teams with clear accountability, operational rigor, and measurable retention and expansion outcomes. Experienced coaching CSMs across the full experience spectrum and creating enterprise health scoring, escalation management, playbooks, and AI-driven risk/health workflows to improve renewal readiness and customer risk mitigation at scale.

Skills

AICRMCollaborationCustomer ServiceJIRAJiraManagementPortfolio ManagementPower BIRisk ManagementSalesforceSlackTableauWritingZendesk

Experience

  • Head of Customer Success, Asset Class · Asset Class05-01-2025

    Recruited to build and lead Customer Success, Professional Services, and Support from the ground up for a private-capital SaaS platform serving institutional investors, family offices, and asset managers — operating within the compliance requirements, audit sensitivities, and financial workflow complexity inherent to regulated investment management environments. Within the first year, transformed a reactive, ad-hoc service culture into a modernized, scalable, revenue-generating post-sale organization—driving GRR from 75.6% to 91.2%, NRR from 75.1% to 97.5%, and maintaining Support First Response SLA above 85% and Time to Resolution above 95%. • Designed and launched a 5-point strategic initiative framework governing CS vision, operational priorities, resource allocation, and cross-functional alignment—now the operating blueprint for the entire post-sale organization. • Built an AI-powered Risk Management dashboard using Claude that synthesizes signals across Salesforce, Jira, Slack, Confluence, email, and industry news into an interactive early-warning tool for attrition and churn risk. • Lead a global team of Customer Success Managers with defined role clarity, career pathing, and performance standards spanning Digital CS, Strategic CSMs, and CS Operations. • Drove a cultural and commercial shift from unlimited free configuration work to a structured, billable Professional Services and feature-request model—creating a net-new revenue stream while freeing engineering to focus on core product innovation. • Identified recurring patterns across the customer portfolio and translated findings into updated playbooks, cross-functional recommendations, and proactive engagement models — closing the loop between individual account insights and team-wide operating improvements. • Architected a tiered onboarding model aligned to customer pricing and complexity tiers, compressing time-to-value and accelerating ROI realization for new customers. • Engineered a company-wide shift from reactive support-driven engagement to a proactive success model built on health scoring, lifecycle playbooks, and predictive outreach. • Created an internal and external product Certification Programs to deepen product expertise across employees and customers, strengthening adoption and reducing time-to-competency. • Established CS operational rigor through standardized processes, service-level boundaries, KPI frameworks, and governance cadences—building a foundation for repeatable, measurable outcomes at scale.

  • Global Director, Account Escalation Management · Forcepoint12-01-2023 – 05-01-2025

    Inherited a strictly reactive, tech-support case escalation program and transformed it into a proactive, account-level risk management function — conducting holistic reviews across the full customer portfolio, including U.S. and EMEA government accounts, to identify churn signals early and drive structured action plans that protected renewal and long-term account health. • Reporting directly to the Chief Customer Officer, I built and led a global team of 20 CSMs and TAMs (Technical Account Managers), including three regional Managers spanning North America, EMEA, and India — redesigning each manager's operating model from reactive case ownership to proactive, account-level risk management, with coaching approaches tailored to the maturity and experience level of each regional team. • Navigated meaningful differences in team maturity across regions — developing the North America team's capacity for complex, long-cycle enterprise engagements while coaching the India team out of a case-driven "say yes to everything" model that was diluting program impact and credibility. • Made a deliberate decision to transition an underperforming regional manager who resisted the new engagement model, then identified and developed a high-potential IC from within the India team to fill the role. • Restructured the program's intake model to eliminate customer-initiated escalations in favor of internally identified risk signals — removing noise-driven requests and focusing the team on accounts with genuine attrition risk. • Built cross-functional alignment across Sales, Product, Support, and Finance — moving high-risk accounts from reactive crisis management to coordinated, resource-backed recovery with executive visibility and shared accountability. • Built and chaired the Red Account Steering Committee, ensuring the highest-risk accounts received coordinated recovery plans with executive sponsorship. • Reduced attrition in escalated accounts by 58% and achieved 63% faster defect resolution by aligning engineering priorities with customer-impact severity. • Earned 100% program satisfaction scores from participating account teams and executive sponsors.

  • Director, Customer Success & Value Realization · Zendesk01-01-2022 – 07-01-2023

    Led Global Risk Management, Strategic Escalations, and CX Governance for Zendesk's enterprise customer base — spanning commercial, enterprise, and public sector accounts — building structured save-and-growth motions during a period of significant organizational change. • Built the “Account Save and Growth” program, combining risk mitigation with expansion-readiness assessment to turn at-risk moments into retention and upsell opportunities. • Partnered with CSMs and Sales to improve renewal readiness and expansion identification across the enterprise portfolio — building early-warning signals into the account health model to surface risk and opportunity ahead of renewal cycles. • Implemented enterprise health scoring and CX governance frameworks, giving leadership a consistent, data-backed view of account health across the global portfolio. • Managed strategic escalations end-to-end, coordinating cross-functional resources and executive engagement to resolve complex, multi-stakeholder customer issues.

  • Enterprise Customer Success Director · Citrix08-01-2020 – 12-01-2021

    Drove cloud adoption and customer success strategy for a portfolio spanning enterprise and public sector accounts during Citrix's strategic shift from on-premise licensing to SaaS and cloud delivery models. • Increased SaaS and cloud adoption by 65% within the assigned portfolio through targeted success planning, migration roadmaps, and executive alignment. • Partnered with enterprise customers across Public Sector, Financial Services, Healthcare, Technology, Manufacturing, Insurance, Telecommunications, Life Sciences, and Energy & Utilities — tailoring success motions, escalation frameworks, and value realization programs to the unique regulatory, operational, and commercial demands of each vertical. • Built structured success plans and executive engagement motions that connected product adoption milestones to measurable customer business outcomes. • Led regular Executive Business Reviews and QBRs with C-level stakeholders, connecting cloud adoption milestones to measurable business outcomes and providing clear visibility into migration progress, platform health, and long-term success planning. • Served as a key bridge between customer needs and product development during a major platform transition, ensuring retention through a period of significant change.

  • Director, Critical Accounts · Salesforce08-01-2015 – 07-01-2020

    Brought in to transform an internal-only Red Account program into a customer-facing escalation model — taking direct ownership of the most highly escalated enterprise relationships until accounts were stabilized and returned to a path to success. Managed average revenue at risk exceeding $20M, while maintaining >95% ARR retention across the escalated portfolio. • Built and led Salesforce's first customer-facing critical accounts program, defining escalation criteria, ownership models, triage protocols, and resolution workflows across all Salesforce clouds and product lines. • Served as the single point of contact for the company's most complex, high-severity customer situations — acting as quarterback across virtual teams spanning Sales, Engineering, Support, Product, Legal, and Finance to drive coordinated resolution. • Led a team of three senior escalation specialists while carrying a personal caseload of the highest-priority accounts, operating as a player/coach across the function. • Launched a global single-customer/multi-issue escalation initiative to resolve high-profile situations involving concurrent technical, product, legal, and relationship risk. • Created and led a Proactive Milestone Management program for top e-commerce and retail customers — identifying at-risk accounts using health scores, account team feedback, and market signals, and deploying white-glove cross-functional engagement models ahead of high-revenue periods such as Q4 holiday, tax season, and healthcare open enrollment. • Developed engagement standards and communication protocols for multi-customer impacting events, including service disruptions, product end-of-life notifications, and compliance issues affecting large portions of the customer base. • Built feedback loops to share escalation findings with Engineering, CS, Support, and Sales — driving continuous product and process improvement from the field.

  • Director, Critical Accounts · Marketo (now Adobe Marketo Engage)05-01-2014 – 08-01-2015

    Launched Marketo’s first company-wide escalation management program, creating the structure and processes for systematic critical-account recovery. • Designed and implemented the company’s first formal critical-accounts program, defining escalation criteria, ownership models, and resolution protocols from scratch. • Drove rapid customer recovery by coordinating cross-functional resources and executive engagement, establishing a repeatable model for at-risk account intervention.

  • Director, Escalation Management · SuccessFactors (SAP)04-01-2013 – 05-01-2014

    Managed global escalation management for SuccessFactors’ cloud HCM platform, reducing attrition risk across the company’s highest-value enterprise accounts during post-acquisition integration with SAP. • Managed the global portfolio of high-risk cloud accounts, building structured intervention plans that reduced attrition risk and protected recurring revenue. • Strengthened executive relationships with key accounts through regular business reviews, transparent communication, and measurable recovery milestones.

  • Principal Technical Account Manager · Salesforce05-01-2011 – 04-01-2013

    Served as trusted technical advisor for a mixed portfolio of 10–15 mid-market and enterprise customers representing ~$10M in ARR — responsible for platform health, adoption, and long-term technical success. • Delivered governance advice, adoption recommendations, and risk identification as part of structured annual Technical Success Reviews. • Provided expert guidance on configuration, administration, and platform best practices, helping customers maximize value from their Salesforce investment. • Monitored adoption and utilization trends across the portfolio, proactively surfacing risk and engaging customers ahead of renewal and expansion conversations.

  • Sr. Principal Technical Account Manager · Siebel Systems / Oracle06-01-2000 – 04-01-2011

    Spent over a decade as a senior technical account leader across Siebel’s CRM platform and through Oracle’s acquisition, building the deep enterprise technology foundation that underpins a career in Customer Success leadership. • Managed complex, multi-year technical account relationships for Fortune 500 clients, serving as the senior technical authority on platform architecture, integrations, and production stability. • Navigated the Siebel-to-Oracle transition, maintaining customer confidence and continuity through one of the era’s most significant enterprise software acquisitions.

Education

  • University of New HampshireB.A.
  • MIT Management Executive EducationExecutive Education, Mastering Design Thinking

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