Sales Team Lead - Player/Coach

Lead from the front . Carry an individual quota and manage your own book of business while continuing to prospect, run discovery, demonstrate value, negotiate, and close new business.

Coach and support a team of Account Executives, helping them strengthen their sales skills, manage their pipelines, develop deal strategy, and consistently work toward their targets.

Act as a hands-on resource during key sales cycles, including joining calls, helping navigate objections, developing negotiation strategies, and supporting AEs through complex deals.

Conduct regular deal reviews, pipeline reviews, call coaching, and skill development with members of the team.

Reinforce Datarails' sales methodology and playbook through both coaching and your own execution in the field.

Help identify performance trends, pipeline gaps, and opportunities for improvement using data and sales metrics.

Support the onboarding and ramp of new Account Executives and help establish strong selling habits from day one.

Share feedback from the field and identify opportunities to improve sales processes, messaging, enablement, and execution.

Partner closely with the Director and VP of Sales on team performance, forecasting, and broader sales initiatives.

Serve as a trusted mentor and culture carrier for the team while continuing to develop your own leadership capabilities.

3+ years of proven success as a quota-carrying SaaS Account Executive, ideally within a high-growth or early-stage environment.

Consistent history of meeting or exceeding individual sales targets.

Demonstrated leadership potential through mentoring, coaching, onboarding, enablement, or serving as an informal leader within a sales organization.

Experience selling complex SaaS solutions to SMB and/or mid-market customers in a high-velocity sales environment.

Previous experience selling to finance teams and/or the CFO's office is strongly preferred; knowledge of FP&A processes is a plus.

Strong deal strategy, discovery, negotiation, and closing capabilities - and the ability to help others improve in those areas.

Working knowledge of modern SaaS sales methodologies such as Challenger, Sandler, Force Management, MEDDPICC, or other value-based selling methodologies.

A data-driven approach to pipeline management, forecasting, and performance.

The ability to balance your own revenue responsibilities with the success and development of others.

A collaborative, low-ego leadership style with a genuine interest in helping others succeed.

Experience thriving in an “up & comer” environment where processes are still evolving rather than relying solely on the infrastructure of an established brand.

A bachelor's degree in finance, accounting, economics, or a related field is a plus.