New Expansion Advisor

Gusto•Chicago, AZ

1d•$89,000 - $116,000•Hybrid

About The Position

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy . About the Role: As a New Customer Advisor at Gusto, you’ll play a critical role in guiding newly signed customers through their first 120 days; ensuring rapid activation, strong product adoption, and early identification of upsell opportunities. This hybrid role blends onboarding, consultative sales, and customer success to drive long-term value for Gusto's SMB customers.

Requirements

3+ years in an Account Executive, Consultative Sales, or Customer Success role. Ideally in SMB tech or SaaS.
Demonstrated success in a KPI driven environment with experience in upselling, cross selling, or owning a quota.
Proven ability to drive adoption, manage a book of business, and influence long-term customer success.
Excellent communication, problem solving, and relationship building skills.
Proficiency in Salesforce and experience with multi-touch outreach tools and strategies
Deep passion for helping small businesses thrive.
Comfortable using AI tools and automation to enhance productivity, decision-making, and problem-solving.

Nice To Haves

Familiarity with sales methodologies like Richardson or Challenger.
Experience in HR, Payroll, or FinTech.
An entrepreneurial mindset with a bias for action.

Responsibilities

Own the early customer journey by driving product activation and onboarding success within the first 120 days.
Execute a structured multi-touch outreach cadence (up to 10 call attempts + email follow-ups) to achieve 6 quality connections per day.
Deliver high-impact product consultations to educate, upsell, or accelerate adoption based on customer needs.
Hit key daily metrics including 60+ calls, 2 demos, and timely follow-ups across your book of business.
Maintain accurate records in Salesforce to track activation milestones and opportunities
Collaborate cross-functionally with support, success, and product teams to continually improve the onboarding experience.
Daily Outreach: Make around 60 dial attempts per day (targeting 6 quality connects using ~10 attempts per connect). Follow up each connect with personalized emails.
Customer Activation & Education: Conduct a minimum of 6 consultative connects daily with new customers. Educate customers on how to leverage the Gusto to meet their business needs. Identify early indicators of potential expansion opportunities.
Collaboration: Update Salesforce with customer progress details and next steps. Participate in daily huddles with your PE to align on new customer statuses and outreach priorities. Work closely with Product, Support, and Sales teams to resolve any adoption challenges.
Results Help drive monthly incremental ARR targets of approximately $30,000 (based on 120 connects per month at an average of ~$250 each).