Inside Sales Representative

Strategy (Nasdaq: MSTR) is at the forefront of transforming organizations into intelligent enterprises through data-driven innovation. We empower people to make better decisions and revolutionize how businesses operate.

We are seeking a motivated Inside Sales Representative (ISR) to help grow and retain our small customer segment for the MCS product. This role plays a critical part in our go-to-market strategy by ensuring tailored attention and sustained engagement across a high-volume portfolio.

• Targeted Migration Outreach: Proactively manage a book of small to mid-sized on-premise accounts (< $50K ARR), engaging them in consultative discussions about their upcoming migration to the Strategy Cloud before the End of Support (EOS) for the legacy on-premise platform in 2028.
• Manage and grow a defined portfolio of approximately 100 existing install‑base accounts within a regional territory.
• Drive renewals, expansions, and upgrades within assigned accounts to capture identified migration and growth opportunities.
• Execute a high-volume, tactical sales approach focused on transactional selling to small cloud customers (Annual Recurring Revenue < $50K
  ).
• Engage directly with customers via phone, email, and virtual meetings to understand their needs, demonstrate product value, and close business.
• Collaborate closely with Partners, Professional Services, AEs, BDRs, and Customer Success to ensure a seamless handoff and ongoing customer satisfaction.
• Track and forecast opportunities in CRM, maintaining accurate pipeline data and activity metrics.
• Contribute to regional growth goals across a total book of 1,200 accounts and $17M in annual recurring revenue (ARR).
• Provide feedback to Sales Operations and Product teams to help refine the MCS product strategy and customer experience.

• 1–3 years of inside sales or business development experience in a SaaS or technology company.
• Demonstrated success meeting or exceeding sales quotas in a high-velocity environment.
• Strong communication, negotiation, and closing skills.
• Comfort with CRM systems (Salesforce or similar) and virtual selling tools (Zoom, Gong, Outreach, etc.).
• Self‑starter with excellent organizational skills and attention to detail.
• Collaborative, adaptable, process‑oriented, and driven to deliver measurable results.
• Clearly articulate the urgency, benefits, and value proposition of migrating, including access to AI‑powered features, reduced maintenance, enhanced security, and compliance with the 2028 End of Support timeline.
• Familiarity with sales methodologies such as Solution Selling and MEDDPICC.
• Incentive‑motivated, ambitious, and highly motivated by financial rewards.
• Focusing on developing their career in Sales.
• We expect candidates to live in the HQ area and come to the office from Monday to Friday.

Strategy is an equal opportunity employer. All applicants will receive consideration for employment without regard to race, creed, color, religion, national origin, gender, sex, sexual orientation, gender identity, disability, veteran status, age, genetic information, or any other legally-protected basis.

Strategy provides reasonable accommodation for qualified individuals with disabilities in the hiring process. If you have any difficulty using our online system and you need an accommodation due to a disability, you may contact us about your interest in employment at applicatio