Enterprise Sales Development Representative

About the Role

We're hiring an Enterprise Sales Development Representative to build and accelerate our enterprise pipeline - partnering directly with Enterprise Account Executives to penetrate named enterprise accounts, and serving as the first point of contact for inbound interest. This is a growth seat for someone with genuine commercial instincts and the hunger to become a full-cycle enterprise seller.

What You'll Do

• Own outbound prospecting into named enterprise accounts through cold calling, email, LinkedIn, and other creative channels.
• Build and execute account plans alongside ENT Account Executives - researching organizations, mapping stakeholders, and sequencing outreach.
• Lead early-stage discovery calls with engineering leaders, FinOps practitioners, and infrastructure decision-makers.
• Carry and beat weekly and monthly targets for qualified meetings booked and pipeline created.
• Participate in deal strategy sessions, pipeline reviews, and customer-facing meetings alongside your EAE.
• Sit in on deal strategy sessions, pipeline reviews, and customer-facing meetings alongside your EAE - learning the full cycle by watching it run.
• Represent PointFive at industry conferences, FinOps events, and cloud infrastructure summits.
• Contribute to market presence through social selling, LinkedIn engagement, and video outreach.
• Track activity, pipeline, and account progress meticulously in CRM, and share field feedback with sales leadership and marketing.

Must-have

• 1-2 years in a sales or revenue-facing role - SDR, AE, Account Manager, CSM, or similar.
• Technically curious - able to learn a complex product and translate technical value into business outcomes for engineering and FinOps buyers.
• Comfortable with cold calling and multi-channel outbound as a core part of the job.
• Strong written communicator - emails and follow-ups that are clear, concise, and move things forward.
• Familiar with CRM tools (Salesforce, HubSpot, or equivalent) and sales engagement platforms.
• Bachelor's degree.

Nice to Have

• Active LinkedIn presence or comfort with social selling
• Exposure to cloud infrastructure, FinOps, DevOps, or AI workload cost management.
• Familiarity with enterprise sales methodologies (MEDDIC, SPICED, Challenger, etc.).
• Experience selling to engineering, infrastructure, or FinOps personas.

Compensation & Benefits

• Base Salary Range: $55,000 - $70,000
• Competitive OTE range: $78,500 - $100,000 with uncapped commission, plus equity
• This is a hybrid role requires 3 days in our Boston office
• Health, dental, vision (yes, all three!), equity in something early-stage and exciting, generous PTO, 401K, meal & commuter benefits, and a team that will actually challenge you.