Simplify Logo


Director of Sales Enablement & Effectiveness

Confirmed live in the last 24 hours



201-500 employees

Digital 401(k) recordkeeping and savings solutions


Compensation Overview

$100k - $150kAnnually

Senior, Expert

Austin, TX, USA + 2 more

Field Sales
Inside Sales
Sales & Account Management
Required Skills
Lead Generation
Data Analysis
  • Bachelor's Degree in Business Management or equivalent work experience.
  • Minimum 4 years of sales effectiveness/enablement experience developing and implementing effective processes, procedures, and programs.
  • Experience in sales & sales management within a B2B setting, preferably in SAAS
  • CRM proficiency in Salesforce and/or Salesloft required
  • Strong project management skills with a focus on outcome-driven ROI
  • Strong proficiency in sales methodologies (challenger selling, MEDPIC, etc.)
  • Experience working in a fast-paced, high-growth, distribution-focused organization
  • Excellent verbal and written communication skills
  • Financial services experience highly preferred
  • Sales training, development, or enablement experience is required
  • Highly motivated sales professional with a proven track record of exceeding KPI goals
  • Proficiency with data enrichment and prospecting platforms such as Apollo IO, Brightscope/Data Discovery, Zoom Info, Lean Data, and/or LinkedIn Sales Navigator.
  • Manage Vestwell’s expanding Sales Development Representative (SDR) team responsible for outbound prospecting across various sales channels, encompassing advisor and plan sponsor sales.
  • Provide coaching to SDRs in sales techniques and best practices. Ensuring individual achievement of key performance indicators such as logged calls, booked meetings, and generated proposals.
  • Manage the lead generation efforts for the SDR team in close collaboration with Sales Strategy & Ops.
  • Own lead routing, enrichment, and processing across the sales organization, including multiple channels.
  • Design comprehensive training and development programs for Vestwell’s sales organization, focusing on sales technical tooling as well as sales development skills for both new hires and ongoing training.
  • Deliver training programs to maximize productivity, efficiency, goal execution and to ensure strong knowledge of Vestwell's systems, processes, and solutions.
  • Provide support for the rollout of new system enhancements and tools introduced by Revenue Operations, Sales Operations, or Sales Strategy teams.
  • Play a pivotal role in change management and business readiness processes, ensuring internal stakeholders within the sales organization are prepared for new tooling and system enhancements.
  • Report on training outcomes, providing feedback to managers and executive leaders regarding trainees' performance and development, and making recommendations for improvement.
  • Utilize reporting and analytics to analyze the sales cycle and train for maximum efficiency.
  • Collaborate directly with Sales Strategy & Ops, Senior Leadership, and Field Sales to develop, roll out, and reinforce strong business processes with sales tools that drive cleaner data, reporting, and revenue growth prediction, as well as more effective management and acceleration of productivity in the field.
  • Work with external consultants/SME as needed for trainings
  • Own ROI of lead generation / prospecting platforms such as Apollo IO, LinkedIn Sales Navigator, and Brightscope.
  • Work cross functionally with RevOps to maintain usage of Lean Data, Salesloft, Salesforce tooling to drive increased conversion rates for net new leads.
  • Execute on lead gen and demand gen strategies set forth.

Vestwell, a digital 401(k) recordkeeper, is an excellent workplace for individuals passionate about empowering small business retirement savings. With a modern API-based platform that offers extensive integrations, configurable solutions, and a commitment to fiduciary oversight, the company stands out in its field for both technology deployment and commitment to compliance. Employees can thrive in a technologically sophisticated environment that prioritizes innovation and effective service delivery in the financial sector.

Company Stage

Series D

Total Funding



New York, New York



Growth & Insights

6 month growth


1 year growth


2 year growth