Head of Sales Effectiveness
Gusto, Denver, CO; New York City, NY; San Francisco, CA, Remote
It’s time to tame the chaos of payroll, benefits, and HR.
We’re looking for a dynamic, strategic leader to run and build our Sales Enablement team. This role is responsible for developing and executing our end-to-end training and coaching strategy for onboarding and ongoing development to empower our Customer-facing sales roles with the skills, knowledge, and processes required to succeed in their roles. Your goal is to help cultivate a Customer-first culture, increase engagement of Sales Managers and Reps, and improve productivity and sales efficiency.
This position will own and manage the end-to-end strategy, design, and operationalization of sales effectiveness programs work including working closely with Sales Leadership and front-line Sales Managers to identify gaps and develop outstanding competencies & behaviors. You’ll design and deliver instructor-led and self-paced training, coaching programs, and other resources to address opportunities and develop our Sales team. This is a highly cross-functional role that partners closely with Product Marketing, Growth & Marketing, People and L&D, Sales Operations, Systems & BizTech, Legal, and other teams.
This role requires strong leadership, strategic thinking and tactical execution, communication skills, knowledge of Sales Development, Direct & Channel Sales, and Account Management, and ability to prioritize and align enablement activities to drive measurable results. Most importantly, passion about the critical role Enablement to maximize revenue growth through a high performing, highly engaged, representative and inclusive Sales team.
Gusto is a modern, online people platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 200,000 businesses nationwide.
Our mission is to create a world where work empowers a better life, and it starts right here at Gusto. That’s why we’re committed to building a collaborative and inclusive workplace, both physically and virtually. Learn more about our Total Rewards philosophy.
Here’s what you’ll do day to day:
- Lead strategy, organization, and execution in standing up the Sales Effectiveness function to empower our Customer-facing sales roles with the skills, knowledge, and processes required to succeed in their roles and improve productivity and sales efficiency
- Partner closely with Sales to become an expert across Customer segments and Sales roles including understanding business goals, strategic initiatives, and sales motions to inform Enablement strategy and priorities (global by default vs bespoke by Customer segment, Sales role - Account Executive, Account Management, Sales Development, etc)
- Own the plan, design, and delivery of Enablement programs (e.g., training calendar, vital few initiatives) to align Revenue leadership on the gaps and priorities across Sales teams including 3rd party training and events and securing associated budget
- Define, roll out, and track certification and assessments role-specific curriculum and paths
- Establish clear guidelines, processes and best practices across intake, development, rollout, maintenance, and deprecation of content and instructor-led/self-paced training
- Develop embedded sales coaching including train-the-trainer programs and performance- and standards-based coaching techniques
- Track and measure the impact of Enablement programs against Revenue goals and priorities, optimize based on feedback, and present results and insights on performance (quarterly business reviews, monthly updates)
- Partner with Learning & Development, Product Marketing, and other Enablement teams (e.g., Customer Experience) to design and deliver Enablement programs, including building and maintaining content, new hire onboarding and on-going instructor-led and self-paced ongoing training, coaching and mentorship, etc
- Facilitate region-specific onboarding sessions for new hires, building and maintaining custom content as needed
- Support internal communications for Sales by delivering relevant, practical information in a timely manner (e.g., product roadmap, legal & compliance, systems & tools), and reinforcing company-wide announcements
Here’s what we’re looking for:
- 10+ years of sales training, coaching and leadership development experience (designing and operationalizing talent enablement), with 2+ years in a SaaS company
- Exposure to different enablement models mapped to different sales models (e.g. higher velocity vs. enterprise, direct and channel sales). Experience with one more more sales methodologies from selection through implementation to optimization
- True passion for sales: you creatively find ways to make sales teams more effective
- Objectivity balanced with growth mindset: a commitment to discovering what works vs. what’s familiar
- Persuasive communicator - you’re a natural storyteller, using data to back up your recommendations and getting cross-functional partners excited to help us deliver on our goals
- Adaptable; you flex naturally between influencing leadership, inspiring those you empower to think big, and rolling up your sleeves to get things done
- Hyper-organized with strong attention to detail; effective stakeholder and project management is the bare minimum and is part of your secret sauce
- You enjoy working with high octane growth companies, where things move fast, people are smart, and processes are quick to evolve - in fact, you’re often the one who moves them
Our cash compensation range for this role is $129,000-197,000/yr in Denver & most remote locations, and $152,000-228,000/yr in San Francisco & New York. Final offer amounts are determined by multiple factors, including candidate experience and expertise, and may vary from the amounts listed above.
Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.
Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. If you need assistance or an accommodation due to a disability, you may contact us at [email protected]
We are Gusto Founded in 2011, Gusto provides payroll, benefits and HR to modern companies. We have offices in San Francisco and Denver, but thanks to our 40,000 small business customers and their employees, there’s a little piece of us in all 50 states. We believe that humans aren’t resources. When we come to work, we don’t leave our humanity at the door. We bring life with us: our feats and friendships, our adventures and aspirations. Great businesses treat us like people, not ID numbers. When that happens, work becomes a source of energy rather than fatigue. It creates a virtuous cycle where life improves work, and work improves our lives. That’s why we started Gusto. Our mission is to create a world where work empowers a better life.
Want to learn more about Gusto? Visit Gusto's website.
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