Director of Customer Success

Max Retail•West Palm Beach, FL

17h

About The Position

Max Retail empowers independent retailers and brands to reach hundreds of millions of consumers through technology that makes multichannel selling as easy as “click, click, sold.” The platform connects sellers to top online marketplaces, automating listings, pricing, and fulfillment. By helping businesses move inventory faster and more profitably, Max Retail fuels a more circular, sustainable retail economy. As we scale from 3,000 to 20,000+ active sellers, we’re doubling down on what makes Max Retail special — human connection and measurable growth. Our Customer Success team sits at the intersection of revenue expansion, relationship management, and enablement, helping retailers list consistently, price strategically, and make Max Retail part of their daily workflow. The Role The Director of Customer Success owns the two outcomes that drive Max Retail’s business: bringing on inventory value and retaining customers through re-listing. Every system you build, every cadence you run, and every CSM you coach is in service of those two numbers, getting sellers to list more inventory, more often, and keeping them active on the platform. You will lead, scale, and systematize a high-performing CSM team that turns onboarded sellers into consistent re-listers, drives active inventory per seller, and reduces churn across cohorts. You’ll build the playbooks, automation, audit rubrics, and data-driven processes that let us scale efficiently without losing the personal touch that defines us. This role reports to the VP of Customer Experience and Operations and partners cross-functionally with Sales, Support, Product, and Marketing, but the scorecard is simple: inventory value brought on, and sellers retained through re-listing.

Requirements

3–5+ years of management experience leading customer success, account management, or sales teams in a fast-paced, scaling environment.
Experience building teams, hiring, ramping, coaching, and exiting people.
Comfortable in HubSpot, Sheets, and BI tools.
Advanced experience with HubSpot or similar CRMs, call recording / audit tools (Fireflies, Gong, or equivalent), and process automation.
Experience owning a CRM as an operational hub.
Strong communication skills, including writing clearly and concisely.
Ability to synthesize seller feedback into actionable insights for the product team.
Ability to deliver direct feedback to the team.
Collaborative approach, partnering well with Sales, Product, Marketing, and Ops.
Self-aware about strengths and gaps, seeking feedback, and willing to be wrong.
Growth mindset.

Nice To Haves

Experience with independent retailers, understanding their thinking, worries, and motivations for listing.
Ability to build reports yourself before asking RevOps to build them.
Ability to create structure from ambiguity, including playbooks, scripts, scorecards, audit rubrics, and dashboards.
Ability to run weekly 1:1s that move performance.
Ability to audit calls, give specific feedback against a rubric, and differentiate between working hard and working on the right things.
Ability to develop the team's bench, with the next team lead coming from inside.
Ownership mentality, taking responsibility for numbers and closing gaps.
Resourcefulness in overcoming limitations like budget or tools.
Willingness to ship a scrappy v1 quickly rather than a polished v2 later.
Ability to share credit and not protect turf.
Seeing cross-functional wins as personal wins.

Responsibilities

Lead, coach, and scale a team of CSMs into a data-driven, high-performing organization.
Run a weekly 1:1 training cadence with every CSM, with format and content that adjusts based on what is actually moving CSM performance.
Run daily team standups grounded in audit findings, coaching to what was found, and surfacing anyone behind pace with a plan to close the gap.
Define success metrics, set clear goals, and hold the team accountable to performance KPIs.
Foster a collaborative, customer-obsessed culture rooted in growth and ownership.
Invest in talent development: train, mentor, and coach CSMs into future leaders of Max Retail, building a strong internal bench that can grow with the company.
Develop a named team lead from within, written development plan covering team lead competencies, training rotation with new CSMs, and a dated book transition timeline.
Own the Q4 (and ongoing) CSM hiring plan in partnership with leadership, tied to sellers-per-CSM ratios and growth targets.
Lead Customer Success’s contribution to Max Retail’s Voice of Customer program, synthesizing seller insights, identifying friction points, and representing the customer perspective in cross-functional planning to inform product development, marketplace strategy, and operational improvements.
Own relisting, reactivation, and engagement strategies to grow payouts and manage churn across seller cohorts.
Develop scripts and playbooks tailored to each customer segment, so every CSM has a clear motion for top performers, mid-tier, and long-tail accounts.
Identify high-value at-risk sellers and deploy targeted outreach to drive retention.
Drive new product adoption, point-of-sale integrations, and staff training.
Drive product adoption and good behavior habits across the CSM team, on-call relisting conversion, pricing strategy adoption, new seller feature adoption, and re-list rate, measured against a documented baseline.
Serve as the HubSpot CRM owner for Customer Success, building workflows, automations, and playbooks to scale communication and performance tracking.
Implement proactive campaigns (listing reminders, first-sale celebrations, price optimizations).
Leverage analytics to pinpoint bottlenecks, seller behaviors, and opportunities for improvement.
Stand up and operate a Fireflies-based weekly call audit process for CSMs against a defined rubric covering all call scripts.
Run a weekly audit cycle, share findings with each CSM, and update the rubric as correlation data dictates, dropping checkbox elements that don’t move outcomes and adding elements that do.
Design and maintain a live performance management dashboard in the Customer Success pit, mirroring Sales’ approach, to display KPIs, celebrate wins, and reinforce accountability.
Integrate key leading indicators, including seller call volume, meeting bookings, listing activity, engagement, fulfillment quality, and onboarding velocity, to forecast outcomes such as return-to-list rate, active inventory value, seller churn, and payout growth.
Use these metrics to drive daily stand-ups and performance reviews, ensuring the team acts early to influence outcomes and maintain momentum.
Partner with Sales, Product, Marketing, and Ops to improve the end-to-end customer journey, including onboarding, listings, seller success funnels, and “surprise & delight” experiences.
Support new partner channel launches by identifying and acquiring inventory that aligns with demand and category strategy.
Collaborate with cross-functional teams to communicate launches and ensure seamless seller onboarding.
Leverage data to drive key assortments with proven sell-through, guiding sellers to list the exact inventory that drives GMV and category growth.
Apply marketplace best practices to curate high-performing assortments, improve sell-through rates, and optimize seller mix across partner channels.
Own key seller and team metrics and continuously optimize: Return-to-list rate (goal: 63–65%+) New Inventory for existing seller targets Days between listings (weekly cadence) Active inventory per seller ($10k+ target at three months live) Seller churn and reactivation success Order cancellation rate reduction CAC payback reduction (toward <6 months) Sellers per CSM efficiency ratio Product adoption and good behavior habits per CSM