Head of Sales, SMB

This leader will be responsible for building and executing a cohesive revenue strategy that spans our high-velocity outbound motions, mid-market and emerging upmarket plays, and our growing account management and expansion engine. Today, approximately 80% of new business is generated via high-volume outbound outreach to SMB and Mid-Market customers, primarily in a phone-based, inside sales environment. As such, the ideal candidate has a proven track record leading large, outbound-centric sales organizations where success is driven by activity, quality of conversations, and disciplined execution.

You will directly manage a team of 6 managers and 55 individual contributors, spanning both full-time employees and offshore BPO team members. Experience partnering with and scaling offshore BPO teams is a strong plus.

A core mandate for this role is to successfully move AtoB up-market while continuing to scale our existing high-velocity engine. This includes hiring and ramping 20+ new Account Executives over the next 6 months, evolving our go-to-market coverage model, and ensuring we have the systems, processes, and culture in place to support sustained growth.

Beyond new business, you will refine and scale our expansion and cross-sell motions and build out a more robust Account Management function focused on multi-product adoption, customer outcomes, and long-term retention.

This is a highly strategic, hands‑on role for a strong systems thinker who understands how people, process, and technology intersect to create predictable, efficient revenue. Experience in or close partnership with Revenue Operations is a significant plus.

• Develop and own the integrated revenue strategy across new logo acquisition, activation of new customers, expansion / cross-sell, and retention.

• Set clear goals, metrics, and leading indicators for each pillar of the revenue funnel (e.g., outreach activity, conversion rates, activation milestones, expansion revenue, NRR/GRR).

• Build and maintain a disciplined forecasting and pipeline management process that drives predictability and accountability.

• Scale and optimize our phone‑based, outbound sales engine that currently drives the majority of new business.

• Ensure teams are executing with excellence on call quality, talk time, sequences, objection handling, and deal progression.

• Implement and refine playbooks, scripts, talk tracks, and cadences designed for high‑velocity environments.

• Continuously improve funnel performance through testing and data‑driven decision‑making.

• Build and execute a strategy to move up‑market, including targeting larger fleets and more complex accounts.

• Recruit, hire, and ramp 20+ Account Executives in the next 6 months, ensuring the right mix of SMB, Mid‑Market, and upmarket capabilities.

• Partner with Marketing, Product, and Rev Ops to align ICP, messaging, packaging, and pricing with our upmarket strategy.

• Develop differentiated sales motions for larger, more complex customers while maintaining our strong SMB foundation.

• Design and refine a structured expansion and cross‑sell motion focused on driving multi‑product adoption and increasing share of wallet.

• Build out a robust Account Management function responsible for ongoing relationship management, strategic account planning, and retention.

• Define success metrics and operating rhythms for account managers (e.g., renewal health, expansion pipeline, NRR).

• Ensure tight coordination between New Business, Account Management, Customer Success, and Support.

• Lead, mentor, and develop a team of 6 sales leaders and 55+ ICs, across both FTE and BPO teams.

• Own recruiting and selection for your org, ensuring we hire talent that matches our low ego, high performance, high standards culture.

• Create and reinforce a culture of brilliance in the basics: consistent activity, crisp follow‑through, clean pipeline hygiene, and high‑quality…