June 17, 2026

Sales Development Representative

Mid • On-site

60,000 - 90,000 USD/yr

Waltham, MA

About the Role

We're looking for a Sales Development Representative to help build and scale our outbound motion. This role is focused on uncovering new business opportunities, facilitating product demos, and guiding customers through a streamlined sales process.

This is not a passive, inbound role. You will be expected to create opportunities from scratch, navigate organizations, and develop messaging that resonates with small business owners and operators in blue-collar industries.

This role is 5x a week onsite in Waltham, MA, with potential for a hybrid schedule after 6 months.
Compensation: $90k OTE ($60,000 base salary + commission)

You Will

  • Drive Outbound Growth: Conduct a high volume of calls and outreach to identify and engage decision-makers and economic buyers.
  • Master the Product: Develop a deep understanding of the SaaS product and its features to effectively communicate value during online product demos.
  • Consultative Selling: Understand prospects' needs and tailor presentations to their specific pain points.
  • Pipeline Management: Maintain accurate records of sales activities and customer interactions in the CRM to ensure forecasting accuracy.
  • Partner for Success: Qualify opportunities and collaborate with the broader sales team on strategy and deal progression.

You Have

Must Have:

  • 1+ years of sales experience in outbound prospecting or business development.
  • Proven track record of meeting or exceeding sales quotas and activity metrics.
  • Excellent verbal and written communication skills with comfort in phone-based outreach.
  • Experience performing product demonstrations and consultations.
  • Ability to commute to the Waltham, MA office.

Nice to Have:

  • Familiarity with the automotive industry, home services, or blue-collar sectors.
  • Experience selling software or working in a high-growth startup environment.
  • Experience using CRM tools (like HubSpot or Salesforce) to manage opportunities.

Interview Process

  • Initial Screen (Lead Recruiter) - 30 min
  • Hiring Manager Interview (Sales Manager) - 45 min
  • Leadership Interview (CRO) - 30 min
  • Reference Checks
  • Completion of the Wonderlic Assessment (20–30 min)

We Offer

  • 100% employer-paid medical insurance
  • Flexible PTO with a 15-day minimum
  • Equity package
  • Generous Parental Leave
  • 401(k)
  • Growth & Learning Stipend
  • WFH Equipment (for home setup)
  • Collaborative culture with career development opportunities

We align our mission of transforming the auto repair experience with opportunities for growth, innovation, and excellence. The hiring process looks beyond credentials and welcomes applicants from diverse backgrounds.

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On-site

Philadelphia, PA

🏢 Summary: Leadership role overseeing Customer Success Managers across enterprise and scaled segments, focused on building scalable account health frameworks and driving proactive retention. The position blends strategic operations, data-driven performance management, and team mentorship in a SaaS environment. The goal is to standardize processes, implement health scoring systems, and improve global customer retention. 🗂️ Requirements: 2+ years managing a Customer Success team or 4+ years as Senior/Lead CSM, Experience managing Enterprise (high-touch) and Scaled/Digital (tech-touch) accounts, Experience conducting QBRs and managing multi-stakeholder accounts, Proficiency using CRM, BI tools, or Excel for health tracking and churn prediction, Experience designing and implementing scalable processes, tools, or playbooks, Ability to define KPIs and manage team performance, Experience building account health scoring models 📃 Skills: CRM, BI, Excel, Gainsight, Vitally, ChurnZero, DataVisualization, Automation, EmailMarketing, SaaS 🏢 Description: About the Role As the Manager of Client Success, you will lead our Customer Success Managers, overseeing a diverse portfolio that ranges from high-touch Enterprise partnerships to high-volume Scaled segments. Reporting to the Director of Customer Success, you will act as the bridge between personalized relationship management and digital-first automation. Your mission is to professionalize Customer Success operations by building a unified "Account Health" framework that works for every customer, regardless of size. You will provide the strategic structure needed to transform informal knowledge into repeatable, data-driven playbooks that drive global retention. You Will Segment the Strategy: Define and iterate on engagement models for Enterprise (high-touch) and Scaled (tech-touch) tiers to maximize efficiency. Build the Health Engine: Develop a standardized Account Health Scoring system that identifies risk across the 1,000+ account base. Operationalize the Knowledge Base: Transition the team from informal collaboration to a structured internal knowledge base and formal playbooks. Drive Proactive Retention: Use leading indicators to trigger outreach before a customer is at risk. Mentor & Measure: Manage day-to-day performance of the Customer Success team, using clear KPIs to drive accountability and professional growth. You Have Must Have: Leadership Experience: 2+ years managing a Customer Success team or 4+ years as a Senior/Lead CSM ready for the next step. Versatile CS Background: Experience managing both Enterprise accounts (QBRs, multi-stakeholder navigation) and Scaled/Digital segments (automation, mass communication). Analytical Proficiency: Experience using data (CRM, BI tools, or Excel) to track health, predict churn, and report on team performance. Systems Thinking: Ability to design scalable processes and successfully implement new tools, workflows, or playbooks. High Emotional Intelligence: Coaching-first management style suited to a collaborative culture. Nice to Have: Technical Literacy: Ability to work with advanced data visualization tools. CS Ops Familiarity: Experience selecting or implementing a CS platform (e.g., Gainsight, Vitally, ChurnZero). Experience with the automotive industry. Interview Process 1. Initial Screen - 30min 2. Hiring Manager Interview - 60min 3. Case Study Assessment - 45min Problem Solving Exercise - 60min 4. Cross-Functional Interview - 30min Completion of the Wonderlic Assessment (20–30min) is required before the end of the process. We Offer 100% remote work environment Medical, Dental and Vision insurance within 30 days 100% employer-paid medical insurance Equity package Flexible PTO with 15 days minimum Generous Parental Leave FSA and HSA options 401(k) Growth & Wellness Stipend WFH Equipment Opportunity to work with the latest technology Collaborative, high ownership culture Opportunities for development and career growth