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Director of Sales Enablement & Effectiveness



Sales & Business Development
New York, NY, USA · Phoenix, AZ, USA · Austin, TX, USA
Posted on Wednesday, May 15, 2024


There are over 30M small businesses in the United States, but only a tiny fraction of them have a workplace savings program in place. As the savings gap in the country widens, it’s imperative that every worker has access to and participates in their company’s savings program, such as a 401(k) or 403(b). We believe that American workers should have easy access to an inexpensive, flexible, and intuitive solution to save for a brighter future.

Unfortunately, prior to Vestwell, small businesses have been neglected and underserved, with expensive, inflexible, poorly designed offerings built on old, mainframe software. Vestwell is changing that, starting with rebuilding the core infrastructure for the modern era.

Vestwell’s north star is to be the engine behind a $30T industry, powering all payroll-deducted workplace savings programs for small-to-midsize businesses, such as 401(k), 403(b), IRA, emergency savings accounts (ESA), health savings accounts (HSA), 529 college savings, and alike.

Vestwell’s focus is to build the most flexible, powerful workplace savings and investment platform, delivered through the hands and minds of their financial services partners with the help of payroll provider partners. The team at Vestwell makes the hard stuff look easy, by combining the expertise of financial advice with the sophistication of a technology provider.

As a result, workplace providers are able to bestow the advice and solution employers and employees have been asking for, while growing and scaling along the way. Employers get a cost-effective solution designed for their needs without all the headaches, and employees get a user-friendly portal that helps them achieve their long-term saving goals.


With backing from leading FinTech investors, as well as a growing team of dedicated professionals of strong industry pedigree, Vestwell is at the forefront of a much-needed change in a 40-year old industry. Our team believes in the mission we’ve set out to achieve and we are working hard to get there. We’re ambitious, honest, thoughtful, and fun.

Who are we looking for?

As the Sales Enablement/Effectiveness Manager at Vestwell, you'll oversee the management of our expanding Sales Development Representative team and lead the continuous training and development of our entire sales organization. Your responsibilities will encompass managing lead generation, enrichment, and routing, along with implementing new technical tools and systems. Collaborating closely with Sales & Revenue Ops, Sales Strategy, and senior leadership, you'll drive change management necessary for the successful introduction of new projects, initiatives, and solutions. Directly engaging with frontline sales representatives, you'll ensure smooth adoption and active engagement with new system builds, technical tools, and product enhancements.

What will you be doing?

  • 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.


  • 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.

The expected salary range for this position is $100K - $150K. Please note that salary bands are based on NY and other similar metro areas and may differ based on where the role is ultimately hired.


We’re a growth stage startup with lots of exciting milestones ahead. We value health and wellness at Vestwell and in addition to a dedicated Employee Wellbeing Committee, we offer competitive health coverage and an open vacation policy. We have adopted a remote-hybrid office policy, but all employees are welcome at our bright, comfortable office with many workspace options in midtown Manhattan so everyone has a setting that is the most productive for them. We provide our team with all the equipment they need (plus a few perks!) to work effectively remotely. Oh, and naturally we have a great 401(k) plan!


It starts the same for every candidate: getting to know the team members through 1 - 2 conversations about Vestwell, your experience, and your interests. Next steps can vary by role, but the usual next steps are a skill or experience screen (e.g. a coding interview for an Engineer, a portfolio review for a Designer, deeper experience call for other roles) which leads to a virtual or in-person interview panel after that if the screens go well. Before making an offer, our interview process concludes with a references check stage for your recruiter to meet with a current or former supervisor and peer. We prioritize transparency and lack of surprise throughout the process.

For your awareness you will only receive correspondence from any other domain not ending in is not our Recruitment team.

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