Sales Team Lead - Player/Coach

Datarails is the financial planning and analysis platform that automates data consolidation, reporting, and planning while enabling finance teams to use their own Excel spreadsheets and financial models. Datarails integrates with the most popular accounting software, ERPs, and CRMs so all your data can be consolidated. Reduce risk, make informed decisions, and ensure stakeholders have the most reliable data at their fingertips. Transform your Excel into a lean, mean, FP&A machine! We are a leading FinTech company with over $100 million in funding and have been awarded #1 most promising global startup by Globes and 65+ leading VCs, as well as one of the best paying and mid-sized companies to work for in NYC by Built In. As a Sales Team Lead at Datarails, you’ll take on a true player/coach role - owning and closing your own business while helping a team of Account Executives elevate their performance and consistently hit their goals. This is an opportunity for a high-performing seller who is ready to take the next step into leadership without stepping away from the craft of selling. You’ll lead by example, coach in the moments that matter, help shape deal strategy, and partner closely with Sales leadership to drive performance across the team. If you have a proven track record of success in SaaS sales, naturally find yourself mentoring the people around you, and want to develop the leadership skills to eventually run a larger sales organization, this could be your next step. What you'll do - 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. What we need - 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.