Enterprise Sales Development Representative

About PointFive

PointFive finds the cost buried inside enterprise infrastructure, from the cloud to coding agents. We pioneered DeepWaste across cloud and data platforms, and we are now doing the same for AI token spend with TokenShift.
Fanatics, H&M, Hertz, Nubank, Citizens Bank and other Fortune 500 companies use PointFive to see and cut what their infrastructure and AI actually cost.

We have raised $96 million, most recently a $60 million Series B led by Accel. Engineering sits in Tel Aviv and our go-to-market team is focused on North America. PointFive Labs, our research arm, publishes original work on how infrastructure and AI actually get paid for.

CRN named us one of the 10 hottest cloud computing startups of 2026, Forbes Israel put us on its Next Billion Dollar Startups list, and Redpoint selected us for its InfraRed 100, its ranking of the private companies shaping the future of cloud infrastructure.

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 EAE partners — 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.

What We're Looking For

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.

Why PointFive

• Founders with a track record — Built and sold IntSights to Rapid7. Backed by top-tier investors with deep conviction in this category.
• Category-defining product — DeepWaste detection and agentic remediation with clear, measurable ROI for both engineering and finance teams.
• Early-stage leverage — Your work directly shapes the product, the culture, and the go-to-market playbook.