Manager, SMB Account Management (Retention)

Block

4d•Remote

About The Position

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn't work together. So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we've embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale. Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We're building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same. The Role The Account Management organization is seeking a results-driven and people-focused leader to manage our Retention Account Management (AM) team. In this role, you will lead a group of Retention AMs responsible for preserving and strengthening relationships with SMB merchants, at critical moments in their lifecycle. You will drive execution against churn reduction and contract renewal goals while fostering a culture of resilience, accountability, and continuous improvement. This role reports to the Head of US SMB Account Management. Retention is a high-skill, high-impact motion at Square. Your team will navigate complex customer conversations, competitive pressure, and competitive pressure to turn risk into renewed partnership. As a leader, you will own the health of the retention business for your segment - driving performance and refining execution standards.

Requirements

8+ years of experience in Sales, Account Management, CSM or a related customer-facing revenue role
3–5 years of direct people management experience in a quota-carrying or performance-driven environment.
Experience managing a team responsible for revenue retention, renewals, or churn mitigation.
Demonstrated success coaching negotiation, financial acumen, and high-stakes customer conversations.
Experience identifying root causes and implementing structured improvements.
Excellent written communication skills, including the ability to synthesize trends and influence cross-functional stakeholders.

Responsibilities

Lead and develop a remote team of 8-10 Retention Account Managers, responsible for churn reduction within the SMB portfolio
Drive retention outcomes through forecasting rigor, pipeline discipline, and elevated negotiation execution across your team
Establish structured performance cadences (1:1s, deal reviews, post-mortems) to reinforce accountability and elevate execution quality.
Partner cross-functionally with Sales, Support, Product, and Analytics to escalate trends, surface churn drivers, and improve the end-to-end merchant experience
Identify patterns in churn risk and translate insights into playbook improvements and enablement opportunities
Serve as a senior escalation point for complex or high-impact merchant situations
Travel approximately once per quarter for team events or cross-functional collaboration