Customer Success Manager – Strategic Accounts

Purple Squirrel Enterprises•Baltimore, MD

2d•$85,000 - $100,000•Remote

About The Position

Purple Squirrel Enterprises has been supporting startups and global firms through growth, change, and expansion for 19+ years. We provide flexible HR and recruiting solutions that allow leaders to focus on strategy while we handle people operations — and this search is no exception. We are exclusively engaged by a high-growth health technology company to help them identify and hire exceptional talent for this role. We are embedded directly with their leadership team, have deep knowledge of the company, the culture, and what it takes to succeed here — and we will be your dedicated recruiting partner from first conversation through offer. This is not a blind submission. When you apply, you are working with a team that knows this opportunity inside and out and will advocate for you every step of the way. Our client is a mission-driven health technology company on a high-growth trajectory. They build integrated software and technology solutions that help care organizations deliver safer, more consistent, and more compliant services to the populations they serve. Their work sits at the intersection of technology, operations, and human care — and the problems they are solving have real consequences for real people. They serve a growing network of specialized care providers across the United States — including intellectual and developmental disabilities (IDD) providers, assisted living operators, and behavioral health programs — helping organizations replace fragmented, manual workflows with technology-guided processes that reduce errors, improve compliance, and give care teams greater confidence in their day-to-day work. This is a remote-first, high-growth company with a lean, high-performing team. They move fast, hold themselves to high standards, and are deeply committed to the mission that drives their work. The Customer Success Manager – Strategic Accounts is one of the most high-impact, high-visibility roles on the Customer Experience team. This is a dedicated, individual contributor role focused entirely on a single strategic partner: a multi-state umbrella organization spanning multiple provider organizations. You will serve as the primary point of contact across the full customer lifecycle — owning the relationship, leading a complex multi-phase implementation across multiple locations and states, driving deep product adoption, and ensuring the customer achieves meaningful, measurable outcomes. This role requires exceptional project management discipline, executive presence, and a genuine passion for delivering an outstanding experience in healthcare settings that serve vulnerable populations. This is not a portfolio role. You will not be managing a book of accounts. You will be solely responsible for one strategic account — owning every aspect of the relationship, implementation, and commercial outcome yourself. Travel: 25–40% travel to customer sites across multiple states is required to support in-person training, go-live events, and executive relationship development. Frequency will vary based on implementation phase and customer needs.

Requirements

7+ years of experience in Customer Success, Strategic Account Management, or an equivalent customer-facing role — preferably within a healthcare-focused SaaS environment
Demonstrated success serving as a dedicated CSM or account owner for a single high-value, high-complexity strategic customer, including navigating multi-stakeholder organizations, multi-site deployments, or multi-entity umbrella structures
Exceptional project management skills with demonstrated ability to plan, execute, and track complex, multi-phase implementations across multiple sites and stakeholder groups
Exceptional communication and executive presence — experience engaging C-level and senior leadership, with the ability to adapt style across frontline staff, site administrators, and executive audiences
Ability to operate at both the strategic and tactical levels — owning executive relationships and long-horizon planning while also rolling up your sleeves for day-to-day implementation details
Comfort with customer success tools and platforms (e.g., HubSpot, Jira, Confluence, or similar)
Ability and willingness to travel 25–40% to customer sites across multiple states (frequency varies by implementation phase)

Nice To Haves

Healthcare industry knowledge — familiarity with HIPAA, DEA regulations, or electronic medical records (e.g., Epic, Cerner, Meditech)
Experience with SaaS platforms in care settings (IDD, assisted living, behavioral health)
PMP certification or equivalent formal project management training
Experience supporting or leading implementations across multi-entity or umbrella-structured organizations

Responsibilities

Serve as the dedicated primary point of contact for a single, high-complexity strategic partner organization spanning multiple providers and states — owning the full customer relationship across software and services
Manage relationships at every level of the customer organization — from executive sponsors and program leadership at the umbrella level to department leads, site administrators, and end-user staff across each provider location
Lead executive engagement including regular cadence calls, Executive Business Reviews (EBRs), data-driven success reporting, and product updates tailored to both the umbrella organization and individual providers
Own the commercial health of the account, including renewal, upsell, and expansion opportunities across the umbrella organization and its member providers
Monitor and drive customer success outcomes including adoption, product utilization, customer health, satisfaction, and measurable ROI — using data to guide proactive interventions and strategic recommendations
Multi-phase project planning, milestone tracking, and cross-functional coordination across internal teams (integrations, technical support, product) and customer stakeholders
Site-by-site rollout planning and go-live sequencing across provider locations and states
Platform configuration and customization across multiple sites and user groups
Quality assurance (QA) and go-live readiness validation per site
Training, onboarding, and adoption support for end users across all provider sites
Post-launch stabilization, ongoing optimization, and continued support
Contribute to the scaled customer experience vision by sharing learnings from this strategic engagement to inform playbooks, processes, and best practices for the broader CX team
Collaborate closely with product and integrations teams to advocate for the customer's needs, surface feedback, and contribute to roadmap priorities informed by real-world use cases
Document interactions, feature requests, and customer feedback to inform roadmap and product development
Represent Customer Success in executive-level engagements and strategic initiatives

Benefits

$85,000 – $100,000 base salary (commensurate with experience) with a benefits package built to support your whole life. Final offer will reflect the depth and relevance of your background.
Medical: CareFirst BlueCross BlueShield — 100% company-paid individual premiums (base HSA plan); dependent coverage available
Dental & Vision: CareFirst — available at employee cost
Company-paid: Life & AD&D, Short-Term Disability, Long-Term Disability
Virtual Care: CloseKnit — 24/7 primary care + mental health, no additional cost
401(k) retirement plan
Lifestyle Spending Account: $50/month, paid quarterly
Perks: Birthday stipend, work anniversary stipend, company swag store
PTO: Flexible, no hard cap — manager approval required
Professional development and learning opportunities
Mission-driven culture — your work directly impacts lives