Pear Suite

Manage client relationships, oversee SaaS platform implementation, provide training and support, and drive customer engagement and retention. | 3+ years SaaS implementation experience, SMB customer support, strong communication skills, and preferably community health or health tech background. | About the role We are seeking a dedicated, proactive, community oriented Customer Success Manager to join our dynamic team. This role is ideal for an individual with a strong background community health work/care navigation and in SaaS software implementation and account management, who is passionate about ensuring client satisfaction and success. As a Customer Success Manager, you will play a crucial role in guiding our clients through the implementation and optimization of our platform, fostering strong relationships, and driving customer engagement and retention. Prior working knowledge of community based practices will ensure success in this role. What you'll do Act as the primary point of contact for assigned clients, providing exceptional support and guidance throughout their journey with our platform. Oversee the implementation and configuration of our SaaS solutions, ensuring seamless integration with clients' existing workflows. Develop and maintain deep knowledge of our platform to effectively address client inquiries, troubleshoot issues, and offer strategic advice. Conduct regular check-ins with clients to review their usage, assess satisfaction, and identify opportunities for further engagement and optimization. Collaborate with cross-functional teams, including Sales and Product, to address client needs and drive continuous improvement. Develop and deliver training sessions and educational materials to help clients maximize the value of our platform. Monitor and report on key performance metrics, including customer satisfaction, usage patterns, and renewal rates. Proactively identify and address potential risks to client satisfaction and retention, implementing solutions to mitigate those risks. Qualifications 3+ year of experience in SaaS software implementation. Must have experience supporting SMB customers. Early stage start-up experience strongly preferred. Background in community health work or health tech is a plus. Strong problem-solving skills and ability to handle complex client issues effectively. Excellent communication and interpersonal skills, with a customer-centric approach. Ability to work independently and manage multiple priorities in a fast-paced environment. Proficiency in relevant software tools and platforms, including CRM systems. Bi-lingual English/Spanish preferred. If you are a results-driven individual with a passion for customer success and a knack for building strong client relationships, we would love to hear from you. Why You’ll Love Working With Us We are fully remote! A mission driven culture that values innovation, collaboration and growth Unlimited PTO Health, dental, and vision insurance Health and Wellness Stipend Professional Development Stipend and Tuition Reimbursement Co-working Stipend The compensation range for this position is $70-85k

Lead strategy and execution for entering and expanding in the payer market, manage sales team, build strategic relationships, and drive revenue growth. | 10+ years in healthcare or health-tech sales or payer strategy with 5+ years leadership, proven multi-million dollar deal closing, deep knowledge of Medicaid/Medicare, and strong executive presence. | About the role The Head of Growth, will own end-to-end strategy and execution for entering, scaling, and expanding in the payer/health plan market. This role will be responsible for revenue generation, market entry design, building strategic health plan relationships, and leading a team of sales professionals. Unlike a pure individual contributor, this role sits at the leadership level and requires both vision and hands-on execution. What you'll do Strategy & Market Entry • Define and evolve Pear Suite’s payer go-to-market vision: target segments (Medicaid, Medicare Advantage, Duals, commercial), geographic priorities, and entry modes (direct contracts, pilots, network partnerships). • Conduct competitive analyses, market sizing, payer gap assessments, and go/no-go decisions for new states or regions. • Forecast and set annual growth targets, quotas, and KPIs for health plan revenue and penetration. Sales & Revenue Generation • Lead the full sales cycle: prospecting, deal qualification, proposal development, negotiation, contract execution. • Secure new health plan clients and expand relationships in existing plans, including upsell, cross-sell, footprint expansion opportunities. Navigate complex payer procurement processes (RFPs, pilots, LOIs, direct contracting). • Collaborate with Finance, Partnerships, Customer Success, and Operations to ensure financially sustainable contract structuring and risk-sharing models. Relationship Building & Thought Leadership • Build and sustain C-suite and VP-level relationships across health plans, including medical leadership, network, innovation, and SDOH arms. • Serve as a public face of Pear Suite: speak at payer / industry events, publish or co-author thought leadership, participate in policy and payer consortiums. • Engage with key stakeholders (state agencies, regulators, tradeshows) to maintain visibility and credibility. Team Leadership & Cross-Functional Alignment • Recruit, mentor, and manage a high-performing team of Strategic Accounts Managers, business development reps, and sales support staff. • Work closely with Product, Marketing, Partnerships, and Customer Success to align product roadmap, messaging, and delivery to health plan needs. • Drive internal enablement: create playbooks, training, collateral, ROI tools, negotiation guides, and sales processes tailored to payers. Measurement & Execution • Implement rigorous tracking of pipeline metrics, win rates, sales funnels, deal cycles, churn, and client satisfaction. • Review performance regularly, diagnose pipeline bottlenecks, and iterate strategies. • Own forecasts, reporting, and accountability to executive leadership. Qualifications • 10+ years of healthcare or health-tech business development, enterprise sales, or payer strategy experience, including 5+ years in leadership roles. • Demonstrated track record closing multi-million-dollar deals with health plans or risk-bearing entities (Medicaid MCOs, Medicare Advantage, Duals). • Deep familiarity with Medicaid, Medicare, managed care models, value-based contracting, SDOH/CHW programs, and payer reimbursement mechanisms. • Experience with long, complex sales cycles, multi-stakeholder decision-making, and navigating procurement processes. • Strong executive presence with ability to build credibility with C-level and senior payer executives. • Experience building, mentoring, and scaling sales teams. • Startup or high-growth experience, with agility and bias toward action. • Willingness to travel (25%–40%) for meetings, conferences, and client engagements. Preferred Skills & Attributes • Experience in payer innovation units, quality/value-based care, or population health risk models. • Experience working in multiple U.S. states and familiarity with state Medicaid markets and regulatory environments. • Strong financial acumen, comfort modeling contract-level ROI, P&L, pricing, and negotiation strategies. • Excellent communication and storytelling skills; ability to articulate clinical, operational, and social value to business audiences. • Ability to thrive in ambiguity and lead through change. What we offer • The compensation range for this position is $130-150k + Commission and Performance Bonus • A mission driven culture that values innovation, collaboration and growth • Fully Remote • Unlimited PTO • Health, dental, and vision insurance • Health and Wellness Stipend • Tech Stipend • Co-working Stipend