Director of Customer Success

The Company

Pear Commerce helps CPG brands get found and get bought. Our technology powers inventory-aware, shoppable experiences across media and digital touchpoints, connecting shoppers to in-stock retailers while capturing full-funnel data and actionable insights. We partner closely with the world’s leading food, beverage, alcohol, beauty, and pet brands to bring these experiences to life, ensuring they launch quickly, perform strongly, and continuously improve over time.

At Pear, Customer Success is at the center of that mission, helping brands turn shopper intent into long-term growth.

The Team

At Pear, we hire the best and then take really good care of them. We want you to grow here, and believe hiring and keeping world-class talent is a true competitive advantage. To be clear, our team is not a family. It’s a group of insanely talented and kind people that work tirelessly (but not like on the weekend or evenings) to make Pear better than it was yesterday.

Pear is a venture-backed startup and, to succeed, you must be comfortable with our approach:

• We focus on alignment so we can act autonomously.
• We are builders and do-ers and we move quickly.
• We ask why because we are curious and like to learn.
• We want the ideal team player: humble, hungry, and smart.
• We are not homogenous. We celebrate diversity.
• We work hard but know when to turn work off.
• We are not afraid of messiness, of change, of moving fast.

The Role

We’re hiring a Director of Customer Success to lead a team that’s already operating at a high level. Pear is recognized across the CPG industry as the standard for what good looks like in our space, which means you’re inheriting strong customer relationships, a capable team, and processes that work.

That foundation opens up the real opportunity: going deeper with customers who already trust us, building the expansion and value story we haven’t fully told yet, and developing a team that’s ready to grow with where the company is heading.

This role reports to the COO. You’ll lead the CSM team and oversee the Implementation org, with executive support on strategic accounts and larger commercial decisions. It’s a hands-on job. You're managing this team, but you're also on the ground with them. No matter the issue, you're in it until it's solved.

You Will Be Responsible For

Team Leadership & Development

• Lead the CSM team and the Implementation org. Set clear expectations, run a consistent 1:1 cadence, and hold the team accountable to outcomes: NRR, GRR, and onboarding velocity.

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• Develop your people. Assess each person’s skills, readiness, and motivation and coach to those specifics. Pear promotes from within when it can, and we want a Director who is invested in what their team becomes.
• Own hiring as the team grows, in partnership with People Ops.

Renewal & Expansion

• Own the renewal and expansion forecast in partnership with Sales and Finance. Track shared north star metrics including NRR and GRR. Know every account: where the risk is, what the upside is, and what you and your team actively doing about both.
• Partner with Sales to sharpen the cross-sell and upsell motion, with clear swim lanes between AEs and CSMs. You own the CS side of that strategy.
• Make value visible throughout the year. Connect the leading indicators in the Pear platform to customer business outcomes, and coach the team to tell that story confidently and consistently.
• Maintain accurate health scoring across the book so the team knows where every account stands at any given time.

Customer Relationships & Escalation Management

• Serve as the executive sponsor on strategic accounts. Available for exec-to-exec engagement when the situation calls for it.
• Own escalations across the book. Know when to resolve them yourself and when to bring in the COO.
• Coach the team to build deep, wide relationships across customer organizations — the goal is trusted advisor, not just point of contact.

Voice of the Customer

• Bring customer context into the business with data behind it. Translate what customers are telling you into actionable insights and use that to tell stories that influence decisions across Product, Marketing, and leadership.
• Partner with Product on feature prioritization, the roadmap, and future innovation, not just flagging where product gaps are creating retention risk.

CS Operations & AI Adoption

• Keep the operational basics tight: account assignments, HubSpot hygiene, health scoring, and onboarding process quality.
• Own the transition from Implementation to ongoing CS. Define what a successful handoff looks like, hold both sides accountable to it, and keep tightening it over time.
• Build a team that uses AI effectively. Find the workflows that make CS smarter, get the team using them, and keep raising the bar.
• Partner with the Head of RevOps on CS tooling, coverage models, and system integrations.

You Have

• 6-8 years in customer success or account management, with at least 4 years managing a CS team. B2B SaaS experience strongly preferred.
• You’ve owned a number. NRR, GRR, a renewal quota. You know what moves it and you’ve been accountable for it.
• You’re an effective leader. The people on your team grow and stay. You develop and coach individuals, not just manage headcount.
• You bring executive presence to customer conversations. Credible, confident, and composed in a room with a VP or CMO at an enterprise CPG brand.
• You’re a data-driven leader. You anchor strategy and decisions in data, use it to tell stories that influence the business, and pressure-test information before acting on it.
• You know when to coach your team through a commercial conversation and when to be in the room yourself.
• Strong, communicative, and collaborative across Sales, Product, and Marketing. You don’t need to win every internal debate to get the right outcome.
• You've implemented AI in ways that have had real, measurable impact on how your team works. You're not chasing the buzz — you have a clear sense of where AI creates leverage today and you stay curious about where it's headed.

Compensation

The base compensation range for this role is $150,000-$160,000. Variable compensation of up to $20,000 is tied to renewals and expansion. Salary is based on a number of factors including geography, experience, and skillset. We also offer:

• 100% of health premiums paid for you and your dependents
• Fully remote work with bi-yearly onsites to meet your colleagues
• 401(k) plan
• $250/month co-working space stipend
• $250 one-time home office stipend
• 20 company holidays and unlimited PTO

Reports to

Chief Operating Officer

Location

Remote