Human Interest is on a mission to ensure that people in all lines of work have access to retirement benefits.

Social Security, our nation’s retirement safety net, is projected to be insolvent as soon as 2035, making employer-sponsored 401(k) plans the primary retirement savings vehicle in the U.S. Nearly half of all working Americans are not saving enough for their future because they are employed by a company that doesn’t offer a retirement plan. Human Interest is changing that by making it affordable and accessible for small and medium sized businesses to offer employees a path to financial independence through retirement savings.

Our values are the guiding principles we use to build solutions for plan administrators and participants. They reflect our point of view on what’s important and what’s right:

In it for customers, autonomous & accountable, outcomes driven, inclusive collaboration, and decisive.

Reporting to the CRO directly, we’re looking for a progressive, forward thinking, passionate sales professional who lives and breathes a growth mindset and wants to be part of growing and developing our revenue driving machine which is the heartbeat of our organization. 

As a member of our Revenue Leadership team; VP of Revenue Team Enablement and Development, you will be responsible for leading the design and development of high impact learning and organizational development programs across our Sales, Partnerships and Implementation teams. The ideal candidate will have a breadth of leadership experience in optimizing organizational effectiveness and provide scalable and culturally relevant approaches that align with Human Interest core values to drive the business forward in exceeding sales goals and expectations.

​​This leader will serve as a direct report and key member of the CRO’s leadership team; they will be instrumental in defining Human Interest’s enablement strategy - ensuring we have the following:  programs, tools and systems and accountability measures in place to 

  • Enable our sellers to deliver a best-in-class experience for our customers; 
  • Ensure our sellers are masters of their craft, continuously honing their skills as sellers;
  • Empower our implementation managers to serve our newly acquired customers effectively;
  • Uplevel our growing team of partner account managers with a continuous learning environment that becomes one of our greatest go-to-market differentiators.

You are a critical member of our Revenue Leadership team, this leader and their team will own all things enablement - reinforcing our Sales Methodology, creating a world-class onboarding program and ensuring we have the right sales and product enablement content and cadence. The AE, PAM, and IM organizations are at the core of our success; onboarding and continuous training and development are key to building a best in class sales team that consistently meets and exceeds expectations. You will work closely and partner cross functionally with product, marketing, sales and all levels of leadership. 

You’re the right fit for this role if you are passionate about accelerating revenue, comfortable rolling up your sleeves, and have a strong bias to insight-driven action. There is ample opportunity to help discover opportunities and scale this team in a rapidly growing company, we want you to help lead it. 

What you get to do every day 

  • Have your finger on the pulse of the business - ensuring that the Revenue team members are  performing: daily inspection, reporting, coaching and mentorship
  • Identify and make recommendations for improvement in the areas of:  training process, efficiency, and productivity; having ownership on building best practices for the Sales organization to follow
  • Determine training requirements by studying sales and marketing strategic plans coupled with current individual performance results to define success metrics accurately and appropriately
  • Create and deliver Sales Training programs that support an effective and motivated overachieving salesforce 
  • Partners with Senior Leadership + Regional Directors to assess training needs and develop ongoing education focused on product knowledge and effective sales techniques that will enable the sales team to maximize revenue potential 
  • Monitor and analyze daily sales team and PAM performance on an individual level to evaluate the effectiveness of training and to design ongoing programs 
  • Work hand in hand with HI’s internal sales coach to identify areas of opportunity and growth to drive excellence and rehab poor performers
  • Inspect and attend sales calls; quarterback closing business and instill best practices in the sales and partner process 
  • Collaborate with partner marketing, RD’s and PAM’s to ensure  the right lead flow is in place to feed the AE’s; if not, come up with other ways for AE’s to hit quota in month
  • Motivate AE’s and PAM’s to exceed objectives through coaching, regular broadcast of results, and creative incentives to help continuously evolve their skillset
  • Own and collaborate with revenue ops to accurately forecast pipeline goals by understanding and analyzing key top of funnel metrics, activities, pipeline quality, and coach on salesforce hygiene 
  • Constant and real-time visibility and reporting to mitigate missed opportunities, i.e. are partner referral leads being missed, leads being ignored in pipeline etc. Action on these misses in real time to drive the business forward
  • Provide weekly forecast (commit/stretch) to CRO & evaluate immediate areas of training opportunities based on monthly forecast attainability 

What you bring to the role 

  • 8 -10+ combined years of experience with proven success in a Sales, Sales Support and/or Enablement Management
  • 5+ years of people management experience
  • 3+ years experience as a frontline Sales leader and/or in a closing role, with detailed and demonstrated understanding of Sales and Partner process from first-hand experience
  • Experience building and iterating an Training, Enablement and Development mindset across a very rapidly growing Sales organization, ideally for a SaaS organization, specifically organizations growing from ~50 individuals to 300+ across multiple locations/remote workers. 
  • Cross-functional team leadership, influence, management, and alignment experience (Enablement, Field roles, executive leadership, Sales Operations, Business Units, Marketing)
  • Experience working with Curriculum and/or instructional designers
  • Strong virtual and live events management understanding and oversight
  • Budget development/planning and management aligned to organizational strategy and priorities
  • Demonstrated mastery of building a high-performing culture of revenue drivers where team members feel challenged, listened to, and rewarded. Strong alignment of their personal and professional goals, with a high level of transparency to ensure team alignment
  • Stellar record of consistent month-over-month performance, able to meet and exceed monthly sales quotas and targets to help scale organizational success and transparency within team, able to pivot or adapt to new strategies to continue to outpace goals and sales expectations
  • Experience working in a high-growth pre-public company and (ideally) transitioning them to a public company.
  • High level of mentorship ability for team members, demonstrated by consistent performance and promotion opportunities, maintaining a high level of professionalism and actionable feedback
  • Strong interpersonal, organizational and Leadership skills able to present to leadership on results of sales performance; translating team performance into easy-to-understand goals, metrics, and benchmarks, aligning on overall sales leadership vision
  • Experience leveraging data to measure, manage, and optimize activity and productivity, reporting on all aspects of pipeline performance and helping bring recommendations and a strong point-of-view
  • Strong Presentation skills, able to present to leadership on results of sales performance with ease 
  • Help oversee usage of sales org systems and tools, including Gong, Outreach and Salesforce.com, collaborating with Revenue Operations, to maximize sales-tech efficacy and ensure the team has what is needed to be successful
  • A growth mindset that values learning and action over perfection, and appreciates teams that follow the values of shared ownership and transparency
  • Comfortable working in an agile, high growth, cross functional environment 

Please feel free to apply to this position even if you do not meet 100% of the requirements listed above.

About Human Interest

We’re a high-growth, Series D-funded company that’s changing the retirement industry. Human Interest is seeking to build a best-in-class product to help small businesses give their employees a path to financial independence. Named one of America’s Best Startup Employers by Forbes, one of the Best Places to Work by the San Francisco Business Times, and a 2021 Top Company by Y Combinator, we’re looking for incredible talent to help us achieve our mission: ensuring people in all lines of work have access to retirement benefits. Human Interest has raised $305M and is backed by leading investors that include TPG (The Rise Fund), SoftBank, Glynn Capital, NewView Capital, USVP, Wing, Uncork, and others.

Inclusive collaboration makes us a better business

We deliberately build processes to create a workplace where all are welcome and accepted. We're proactive and purposeful in prioritizing diversity and inclusion internally not only because it's the right thing to do, but also because we believe it's the only way to effectively create products and services that can be truly helpful to all people.

Human Interest is an equal opportunity employer. All applicants will receive consideration for employment without regard to race, color, religion, sex, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran or military status, pregnancy, or any other characteristics protected under federal, state, or local laws.

Human Interest employees must adhere to the Company’s security policies and Code of Ethics. 

Please note Human Interest does not accept unsolicited resumes from any source other than directly from candidates. We will not consider resumes from vendors including and without limitation search firms, staffing agencies, fee-based referral services, and recruiting agencies.

Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.


We comply with CCPA guidelines. 

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