Sr. Customer Success & Enablement Manager

Reports to: CEO

Team: Customer Success

ABOUT PINNACLE

Pinnacle offers Pascal, an AI-powered coaching platform that sits inside the flow of work. Pascal acts as a personal thought partner for every employee: surfacing insights, driving accountability, and helping people grow every day. We work with forward-thinking HR and L&D leaders at mid-market and enterprise companies who want to move beyond point-in-time training and deliver lasting behavior change at scale.

We are early, intentional, and growing fast. This is a high-impact role for an experienced CS, change management, or learning professional who wants to make their mark at a company where the work genuinely matters.

ABOUT THE ROLE

This is not a traditional Customer Success Manager role. We are not looking for someone who manages tickets, writes up meeting notes, and tracks health scores on a spreadsheet. We are looking for a strategic operator who thinks and acts like a consultant to our clients, someone who can walk into an executive room, understand the organizational dynamics at play, and help HR and business leaders drive meaningful change through Pascal.

You will own the post-sale customer journey from implementation through expansion, driving engagement and adoption, building executive relationships, and ensuring customers realize measurable value from Pascal. You will work directly with the CEO, who leads Pinnacle's sales efforts, and will have high visibility across the business.

The most important part of this role is driving engagement and utilization with our product - working with your client counterparts to identify opportunities to plug in Pascal to existing people processes, designing change initiatives, drafting comms, etc.

Another critical part of this role is building and systematizing the CS function itself. You will inherit a set of existing processes and customers and be expected to automate, and improve them, using AI tools and no-code/low-code platforms to reduce manual work and create a scalable, repeatable customer experience.

WHAT YOU'LL DO

Drive adoption as a trusted strategic advisor

• Serve as the relationship owner for a portfolio of customer accounts, the person champions call when they want to think through something.

• Facilitate stakeholder alignment inside customer organizations, including HR leadership, managers, and executive sponsors.

• Design adoption programs and custom communications tailored to each customer's organization: rollout comms sequences, manager enablement sessions, and communication cadences that carry momentum past the initial launch.

• Diagnose organizational resistance (skeptical managers, change fatigue, competing initiatives) and build a plan that works.

• Help customers build the internal change management muscle they need to drive adoption.

Own the day-to-day customer experience

• Serve as the primary point of contact for all active accounts. For enterprise clients (e.g., HubSpot), this means weekly check-ins and weekly reporting; for the broader portfolio, monthly check-ins and monthly reporting.

• Deliver structured executive reporting that connects Pascal engagement data to business outcomes, active users, adoption trends, benchmark comparisons, and ROI storytelling.

• Run QBRs, executive business reviews, and onsite visits for key accounts, in partnership with the CEO.

• Monitor engagement data across the portfolio to proactively identify at-risk accounts and intervene before utilization drops.

Build and systematize the CS function

• Implement automation opportunities across the CS workflow, using AI tools and no-code platforms (e.g., Claude Skills, Zapier, , HubSpot workflows) to reduce manual effort and improve consistency.

• Build and iterate on onboarding templates, email sequences, and training materials so every customer gets a consistent, high-quality launch experience, without it requiring heavy lift each time.

• Create and maintain the reporting infrastructure: standardized templates, automated data pulls, and dashboards that make it easy to track account health and communicate value at scale.

WHAT WE'RE LOOKING FOR

Required — we will not compromise on these:

• 5+ years in a role where you owned a complex external or internal stakeholder relationship end to end with HR or L&D stakeholders (e.g. implementation, driving adoption, stakeholder engagement, data & reporting, renewal). Could be an experienced HR tech CSM, an internal communications leader, or a learning & development leader.

• Genuine AI fluency. You actively use AI tools in your day-to-day work, you understand their capabilities and limits, and you can help customers think through AI adoption credibly. See how we think about that here:

• Hands-on automation and process-building experience from scratch. You have built workflows using agentic tools (OpenClaw, Claude Skills & MCPs, etc.) and/or tools like Zapier, HubSpot, , or similar. You know how to identify manual work and replace it with scalable systems.

• Change management chops. You understand how organizations resist and accept change, and you know how to work with that reality rather than against it.

• Strong executive presence and communication skills. You are comfortable presenting to HR leaders, CHROs, and C-suite stakeholders and you hold your ground in those conversations.

• Strong written communicator. You can ghostwrite in someone else's voice, draft comms that make change land, and stand up a rollout announcement or FAQ without needing a marketing team.

• Extreme ownership mentality. You move fast, figure things out independently, and do not wait for the process to be handed to you. You are comfortable being the one who creates the process.

NICE TO HAVE

• Experience in HR technology. You know the players, you understand the buying process, and you can speak the language of HR leaders.

• Experience with basic data analysis

• Consulting, MBA, or client-services background. You are used to framing problems strategically and presenting recommendations to senior stakeholders.

• Experience at an early-stage startup where you built something from scratch, not just maintained it.

• Familiarity with tools like Claude Cowork, Linear, HubSpot, , Notion, Zapier, or similar CS-adjacent platforms.

WHY JOIN PINNACLE

• You will have a direct impact on a product that genuinely changes how people grow at work.

• You will have real ownership over a portfolio of meaningful accounts, over the CS function itself, and over how Pinnacle shows up for its customers.

• You will work directly with the CEO and have a front-row seat as Pinnacle scales.

• You will be at the center of the intersection of AI, coaching, and organizational change — one of the most interesting spaces in enterprise SaaS right now.

Pinnacle is an equal opportunity employer. We welcome candidates from all backgrounds and are committed to building a team that reflects the diversity of the customers we serve.