Sr. Manager, Mid-Market Sales (West)

Job Description

We are seeking an experienced sales manager to help lead our mid market sales efforts. This role will manage and grow a team of Regional Sales Directors, that sell health & lifestyle employee benefits, (HSA/FSA/HRA/MTA/LSA/COBRA/Commuter), to HR buyers and benefits insurance brokers. You and your team will focus on selling to the Mid-Market (100-2,000) segment, and be responsible for carrying out the Lively sales playbook. You will make adaptations in real-time to scale our repeatable and successful sales motions that include prospecting and qualifying to closed-won deals. You will work closely with other leaders to establish and improve our broker channel sales processes, and forecast our sales pipeline. 

The ideal candidate will have owned the management of their team’s sales pipeline, forecasting, and led a team that outperforms. You have proven experience selling through benefits brokers, and overseeing sales organizations. Additionally, you have proven experience managing a sales team as part of a growing company, and are excited about the coaching and mentoring that it requires. You display empathy to work with a variety of sales professionals, can manage each sales rep to exceed quota, and can develop a set of processes to optimize your team’s time. You know the nuanced details of an HSA, FSA, and other employee benefits and are excited to share their value.

Responsibilities:

• Managing sales reps to meet and exceed their quota
• Collaborating with sales reps to establish and execute against a territory plan
• Conduct weekly territory reviews and pipeline reviews
• Ensure quality data within each rep’s opportunities
• Analyze KPIs on a regular basis and create performance reporting for management
• Mentor and coach on various elements of the sales process including conducting discovery and objection handling
• Teach reps how to deepen relationships and get into brokers they don’t have relationships with yet
• Measure and manage rep activities to ensure they are spending time on the things that maximize their value
• Manage, analyze, and report on budget expenditures
• Establish and continuously improve sales processes as needed to streamline the collective team’s time
• Share best practices across the team to highlight victories and minimize challenges
• Work closely with Revenue Operations and Marketing for sales education and ongoing training
• Proactively identify and develop growth opportunities in various markets
• Travel is expected to be 30-50%

Skills & Experience: 

• 10+ years of sales-related experience, preferably at an employee benefits carrier, with at least 5+ years in a people management role 
• Proven track record of leading high performing sales teams and performance management
• You have proven success in value selling and you are keen on applying a consultative sales strategy as part of our sales motion. Familiarity with the Sandler Sales methodology is a plus
• Must be adept working in Salesforce, and comfortable working with a variety of other digital sales and sales management/outreach tools
• Demonstrated excellence in project management, presentation, and leadership skills
• Must have excellent written and oral communication skills, and ability to effectively influence key decisions makers
• Must have demonstrated success working with various stakeholders, including complex contract negotiations
• A good sense of humor and a down-to-earth personality. We work hard, have fun, and treat people with respect
• Bachelor’s degree from an accredited college or university preferred, but not required

This position has a competitive base salary, as well as additional variable compensation based on team performance and goals. OTE expected to be around $240k - $300k, with uncapped incentive.