• Job Description

  Req#: 1105
  This is a high-volume position that we fill often. By applying, you'll be added to our priority list for upcoming openings. Thank you for your interest in joining Leap - let's stay in touch!
  
  Hiring Locations: Must be based in either the Chicago, IL or Baltimore, MD markets
  
  About Us
  
  At Leap, we're on a mission to transform the home improvement industry - and we want you to be part of that journey. We're proud to be recognized on the Inc. 5000 and Inc. Regionals lists for 5+ consecutive years, reflecting sustained growth driven by innovation, strong execution, and an incredible team. We build technology that helps contractors work smarter, scale faster, and deliver better experiences to their customers.
  
  When you join Leap, you'll work alongside curious minds, bold innovators, and thoughtful risk-takers who care deeply about doing great work - and doing it together. Our culture is transparent, supportive, and grounded in approachable leadership. We actively listen to our employees through semi-annual engagement surveys, maintain a strong eNPS score, and consistently act on feedback to improve what's working and where we can do better. We believe great work happens when people are supported outside of work, which is why we offer comprehensive benefits and wellness resources for you and your family.
  
  Take the Leap today and help shape what's next.
  
  Position Overview
  
  We are seeking a results-driven, customer-focused Senior SalesPro Onboarding Specialist responsible for driving customer adoption, accelerating time-to-value, and ensuring successful product launch and early-stage account health.
  
  This role blends structured project execution, consultative onboarding, and proactive risk management. The ideal candidate is confident leading client-facing conversations, managing multiple complex projects simultaneously, and holding customers accountable to timelines and outcomes.
  
  This is not a passive training role. This is an ownership role. You will serve as the quarterback of the onboarding experience - ensuring customers launch successfully, adopt effectively, and transition smoothly into long-term partnership.
  
  Responsibilities
  
  • Drive Customer Adoption & Time-to-Value
    • Technical account builds and configuration
    • Lead structured, outcome-focused onboarding engagements
    • Deliver engaging, role-based training aligned to customer business goals
    • Reinforce best practices to drive behavioral change across sales teams
    • Ensure customers are prepared operationally and technically for go-live
  • Own Structured Project Execution
    
    • Build and maintain detailed onboarding project plans
    • Establish clear timelines, milestones, and customer deliverables
    • Drive accountability with customer stakeholders to prevent project delays
    • Maintain consistent communication cadence and documentation
    • Track time accurately and manage utilization effectively
  • Launch & Hypercare Management
    
    • Own customer readiness for go-live
    • Monitor adoption, system usage, and early health indicators post-launch
    • Identify and address gaps during the hypercare period
    • Proactively escalate risks with mitigation plans
    • Partner with Customer Success to ensure smooth transition post-hypercare
  • Stakeholder & Executive Communication
    
    • Identify and engage 2-5 key stakeholders per account
    • Lead milestone reviews and launch readiness conversations
    • Communicate risks, dependencies, and expectations clearly and professionally
    • Navigate stalled projects and re-engage decision-makers effectively
  • Scope & Services Alignment
    
    • Clearly distinguish onboarding services from Professional Services engagements
    • Identify out-of-scope requests and route appropriately
    • Protect company revenue while maintaining customer trust
    • Collaborate with Professional Services for expansion opportunities
  • Cross-Functional Collaboration
    
    • Partner with Sales, Customer Success, Product, and Support teams to ensure alignment
    • Provide structured feedback on common onboarding challenges
    • Contribute to continuous improvement of onboarding processes and playbooks
  
  Qualifications
  
  • 4-5+ years of experience in SaaS onboarding, implementation, or customer-facing delivery
  • Experience managing multiple concurrent client projects
  • Experience driving customer adoption and behavioral change
  • Strong project management and organizational skills
  • Experience navigating difficult client conversations and managing expectations
  • Education:Associate or Bachelor's degree in a relevant field or equivalent work experience
  
  Preferred Qualifications
  
  • Experience in CRM or sales enablement platforms
  • Experience in startup or high-growth SaaS environments
  • Familiarity with structured project management methodologies
  
  Success Metrics
  
  • On-time and on-scope customer launches
  • Strong post-launch adoption and health scores
  • Positive client feedback during onboarding and hypercare
  • Minimal scope leakage into unpaid work
  • Accurate time tracking and strong utilization performance
  • Low onboarding-related churn
  
  
  Benefits
  
  We believe in supporting our employees holistically - your health, financial well-being, time to recharge, and overall happiness matter to us. Here's what you can look forward to:
  
  • Affordable Health & Wellness Coverage - comprehensive and competitive benefits package, starting the first of the month following your hire date..
  • Invest in Your Future - 401(k) company match to help you build financial security.
  • Time to Recharge - We believe time to rest and recharge matters. Leap offers a Flexible Time Off (FTO) policy, 10 paid sick days, and 8 paid company holidays.
  • Comprehensive Employee Assistance Program (EAP) - resources to support your mental health, financial well-being, and everyday challenges.
  • Exclusive Discounts with LifeMart (via ADP) - save on groceries, restaurants, entertainment, pet insurance, cell phones, child care, and more!
  • MoveSpring Wellness App - stay active and engaged with company step challenges, workout content, meditation tools, and wellness blogs for a healthier you!
  • Culture & Team-Building Activities - we love to connect, celebrate, and grow together through team events, fun challenges, and company traditions like our Annual Summit!
  
  
  Join us and experience a company that truly invests in YOU!
  
  Leap is an Equal Employment Opportunity and Affirmative Action Employer. We are committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants and teammates without regard to race, religion, color, sex, gender identity, sexual orientation, age, non-disqualifying physical or mental disability, national origin, veteran status or any other basis covered by appropriate law. All employment decisions are made based on qualifications, merit, and business needs.

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