Work at a Startup

Who We Are

At Clearstep, we believe healthcare should be easy. We build technology that enables patients to find the exact right care while also allowing healthcare systems to tackle the most pressing capacity issues in their organization. As the most prevalently adopted self-service, AI triage platform (both in the federal and commercial spaces), Clearstep is on a mission to improve outcomes for patients and providers alike. Clearstep reaches patients in all 50 states, having directed millions of patients to the best care at the right time.

Why Work With Us

You should consider joining us if you are looking for mission-oriented work, are driven to improve the healthcare experience, are excited to catalyze change in a complex industry, and want to build a solution that can help your friends/family easily navigate healthcare. Clearstep provides abundant opportunities for individual career growth in addition to giving you the chance to directly impact the success of an innovative market leader in the AI healthcare industry.

Core Responsibilities

CRM Management & Data Integrity:

• Own and manage the CRM (HubSpot), ensuring it is up-to-date, reliable, and accurately reflects the sales pipeline.
• Track and report on key sales metrics, ensuring data quality and actionable insights.

Sales Process & Pipeline Accountability:

• Introduce structure and discipline to the sales process, ensuring pipeline visibility and accountability.
• Oversee weekly sales meetings with sales and marketing teams, driving alignment and progress on key initiatives and prospects.

Sales Enablement & Asset Development:

• Generate and maintain sales assets (decks, one-pagers, battlecards, case studies) for all stages of the sales journey and for various prospect personas.
• Develop and maintain a comprehensive sales playbook for BDRs, contractors, and internal stakeholders.

Sales Contractor Coordination:

• Serve as the main point of contact for sales contractors, ensuring alignment with company processes and objectives.
• Onboard and train new sales contractors, providing ongoing support and feedback.

Cross-Functional Collaboration:

• Coordinate with product, customer success, and engineering teams to ensure seamless handoffs and alignment on customer needs and product updates.
• Support marketing in tracking the effectiveness of campaigns and events, ensuring lead quality and pipeline health.

Forecasting & Reporting:

• Prepare and deliver regular sales forecasts, pipeline reports, and performance dashboards for leadership and board reviews.
• Identify trends, risks, and opportunities within the sales pipeline and recommend actions.

Sales Calls & Sales Self Prospecting:

• Help handle initial sales demo calls and own certain accounts in the pipeline
• Help bring in new prospects via self prospecting and attending events / conferences on behalf of the company.

Process Optimization:

• Continuously evaluate and improve sales processes, tools, and workflows to drive efficiency and scalability.
• Implement best practices for lead management, opportunity tracking, and deal progression.

Requirements

Experience:

• 4+ years in sales operations, sales enablement, or a similar role in a B2B SaaS environment.
• Skills:
• Strong proficiency with CRM platforms (HubSpot preferred).
• Excellent analytical and reporting skills, with a keen attention to detail.
• Experience building and maintaining sales assets and playbooks.
• Strong project management and organizational skills.
• Ability to coordinate multiple stakeholders and drive alignment.
• Excellent communication and interpersonal skills.

Personal Attributes:

• Proactive and self-motivated, with a passion for building scalable sales processes.
• Comfortable working in a fast-paced, lean, and evolving environment.
• Ability to translate ambiguous requirements into clear, actionable plans.
• Collaborative mindset and a strong team player.

Nice-to-Haves

• Experience in healthcare or technology industries.
• Familiarity with marketing automation and lead generation tools.
• Experience supporting a distributed or remote sales team.
• Knowledge of contract management and deal desk processes.

Compensation & Benefits

• Competitive salary, commensurate with experience
• Stock compensation plan – you’ll be a Clearstep co-owner
• Health insurance
• 401k with 4% match
• Flexible work schedule and unlimited PTO
• Monthly WFH and Health stipends
• Fully remote with one day a week of in-person time recommended (preferred location: Chicago or NYC)
• Strong emphasis on collaborative learning and career development