Director, Sales - TELS

Direct Supply•Milwaukee, WI

28d

About The Position

Direct Supply is building the future of healthcare technology with industry-leading products, solutions and platforms to help improve the lives of millions of seniors and those who care for them. In the Director, Sales – TELS position, you’ll lead a high-performing team of inside and outside sellers to drive customer success, satisfaction, growth, and retention across our TELS business. As a member of the TELS Senior Leadership Team, you will collaborate in setting overall business strategy, represent voice of customer, and influence go-to-market execution. This leader will play a critical role in fostering long-term customer value with an AI-powered consultative model, selling to Senior Living owners and operators including maintenance, capital, asset management, environmental and facility operations teams, from the building-level maintenance directors to the executive level decision makers. Skills Needed: Drives Accountability & Results – Sets clear goals and ensures team members deliver top-notch results. Uses data and tech to boost accountability, pushing everyone to excel individually and as a team. Leads & Inspires Partner Owners – Ignites Partner Owners’ passion and purpose. Boosts Partners to peak performance while operating at the top of their license. Attracts and develops top talent and builds an environment that fuels innovation. Demonstrates Influence & Organizational Savvy – Wields influence with a masterful understanding of organizational dynamics, effortlessly navigating the complexities to shape outcomes and drive strategic alliances. Applies AI and Technology – Identifies opportunities to boost efficiency and add value using AI and tech. Embraces and applies digital innovations and tech solutions to build business. Eagerly learns and integrates new technologies where they matter most. Demonstrated ability to lead and scale consultative sales teams in complex B2B environments. Strong fluency in CRM platforms and sales analytics to drive strategy, insights, and forecasting. Deep experience selling into multi-site, enterprise-level accounts, with a focus on customer lifetime value and expansion.

Requirements

Bachelor’s degree required; MBA or advanced degree preferred.
Minimum of 7 years of progressive leadership experience in sales, account management, or customer success—preferably within SaaS, healthcare, or senior living.
Demonstrated success leading high-performing sales teams to achieve aggressive growth targets, with proven ability to manage multi-site or national accounts.
Strong experience in data-driven sales leadership, with deep CRM fluency (e.g., Salesforce or equivalent), pipeline forecasting, and account segmentation strategies.
Familiarity with AI-enabled sales tools and performance analytics to inform strategy and enable consultative, insights-based selling.
Exceptional ability to collaborate cross-functionally with executive stakeholders, with a history of aligning customer needs to scalable go-to-market strategies.
Ability to travel by car and/or plane up to 25%.

Nice To Haves

Experience working in senior living, healthcare, or SaaS preferred
Experience collaborating with enterprise-level stakeholders across national or multi-site customers
Familiarity with sales planning, forecasting, or account-based growth models is a plus

Responsibilities

Lead, coach, and scale a high-performing team of inside and outside sellers focused on delivering revenue growth, customer retention, and expansion across the TELS portfolio.
Define and drive the sales strategy, integrating AI-powered insights, CRM data, and consultative selling to improve performance across the sales funnel.
Partner cross-functionally with Product, Marketing, Engineering, and Supply Chain to shape go-to-market strategy, aligning sales execution with customer value and business priorities.
Act as a senior voice of the customer, influencing platform development, customer journey improvements, and solution innovation through feedback and market intelligence.
Develop and operationalize key performance metrics and account planning processes, ensuring team accountability and strategic focus across multi-site and national accounts.
Collaborate with senior leaders across Enterprise Sales and Business Units to support strategic initiatives, team enablement, and shared growth goals.