Head of Sales Insights and Operations

| Greater Denver Area

Gusto is on a mission to create a world where work empowers a better life for all Small Businesses. We have grown to more than 60k customers -- 1% of all companies in the US -- via our unique customer-first product & services and lower distribution costs that enable us to get in front of customers that historically were unprofitable to acquire in our industry. Our acquisition programs combine the best of SaaS and business services capabilities in a B2B high-volume, data-rich environment.

We are looking for a uniquely talented, hungry, and experienced leader to lead our Sales Insights & Operations organization.

Today, we have strong, growing, passionate direct and indirect sales teams that help small and medium businesses discover and adopt Gusto solutions. We need someone to help us continue to innovate and grow smarter, faster, and bigger with deeply insightful strategy, analytics, and enablement about our unique model.

As the leader of Sales Insights & Operations, you will provide actionable insights to the Heads of Sales, Marketing, and CX to improve lead generation, acquisition, and onboarding efficiency. For Sales, you will drive organizational, process, and technological strategies to improve conversion, maximize cost-effective acquisition, and deepen customer relationships. You will manage a team of business partners and analysts; and be the right hand of sales leadership.

More about you
On your first day, we’ll expect you to have:

  • 3-5 years experience in strategy and operations at a sales organization of more than 100 team members, with a proven track record of improving the efficiency and effectiveness of business processes essential to sales force productivity.
  • Experience scaling sales strategy and operations in a “medium velocity” model including inbound and outbound (inside) tactics.
  • 7 to 10 years in the software industry/related business experience
  • Strong leadership skills: you know how to coach and mentor your team members, know how to challenge ideas effectively, and know how to collaborate in a manner that drives decisions and outcomes for the business
  • Expert data & analysis skills: you know what to questions to ask, how to capture data, what the data says, and what actions we can take based upon the results. You will leverage the tried and true, and when beneficial, be creative and inventive with how to truly measure success, understand drivers, and find opportunities to improve.
  • Experience managing requirements for business technology platforms, including how CRM platforms like Salesforce and related technology tools are best leveraged in an inbound sales model.
  • Professional consultative skills: you can bring insights to partners with executive presence and clarity, enabling them to take bold, impactful action and habituating them to seek your strategic advice.
  • A results- and efficiency-oriented mindset, balanced with adaptability and a positive attitude.

And it’s admired, but not required if you have:

  • Experience with data definitions and requirements
  • Direct sales experience
  • SQL and other analytical skills
  • A track record writing or presenting on effective methodologies to create efficient sales organizations, go-to-market models, and metrics
  • Change or program management training 

More about our team
Our five-person Sales Insights & Operations team is staffed with committed, bright, dedicated people helping our sales organizations understand current performance, forecast the future, and improve process for our Direct and Indirect Sales channels. The team is a part of our broader Insights & Operations team, which helps our business leaders across Marketing, Sales, & Customer Experience set and achieve the right goals via strategy, operations, and technology.

About Gusto:
Gusto's mission is to create a world where work empowers a better life (what we believe). Gusto has built the first modern all-in-one people platform, bringing together Payroll + Benefits + HR + Employee Onboarding, under one roof. The company is currently processing several billion dollars in payroll, and serves over 60,000 businesses nationwide (which represents over 1% of all employers in America). Customers love the product (NPS of 75+) and spread the word on social media. The company has over 500 employees and is located in San Francisco & Denver. Gusto is funded by Google Capital, Kleiner Perkins, and General Catalyst, as well as the CEOs/Founders of Instagram, Stripe, Nest, PayPal, Yelp, Mint, Shopify, Yahoo, Thumbtack, Dropbox, and Eventbrite, among others.

  • Press: www.gusto.com/press including a broadcast interview
  • Gusto video campaign: For HR People Who Do Everything
  • Our investors: www.gusto.com/investors
  • Customer spotlight: https://gusto.com/customers and public customer comments (from Twitter)
  • Company values: www.gusto.com/values -- these guide all aspects of how we run the company. We have big ambitions, but being proud of how we achieve those goals matters to us just as much as reaching our potential.
Read Full Job Description
Apply now
loading ...


1201 16th St, Suite 350 , Denver, CO 80202
1201 16th St, Suite 350 , Denver, CO 80202

What are Gusto Perks + Benefits

Health Insurance & Wellness Benefits
Dental Benefits
Vision Benefits
Health Insurance Benefits
Retirement & Stock Options Benefits
Company Equity
Vacation & Time Off Benefits
Generous PTO
Perks & Discounts
Commuter Benefits
Company Outings
Daily Meals Provided
Stocked Kitchen
Happy Hours
More Jobs at Gusto24 open jobs
All Jobs
Design + UX
Dev + Engineer