Inside Sales Representative at Pointfive

ABOUT POINTFIVE PointFive is the Cloud & AI Efficiency Engine trusted by engineering and FinOps teams at companies like Fanatics, H&M, Bridgestone, and Hertz. We created the category of Cloud & AI Efficiency Management — because legacy tools only show what you spend. PointFive shows what you’re wasting and helps you fix it. Customers see ROI in as little as 10 days, 1,200%+ average ROI, and a 4.9 rating on G2. Founded by the team behind IntSights (acquired by Rapid7) and backed by Index Ventures, Salesforce Ventures, Entree Capital, and Sheva Capital, we’re a fast-growing Series A company building to win one of the most important problems in modern infrastructure. The Role We're hiring an Inside Sales Representative to accelerate our enterprise pipeline and own our inbound SMB business. You'll partner directly with Enterprise Account Executives to penetrate named enterprise accounts — going deeper and staying longer than a typical BDR. When SMB opportunities come inbound, you own them end-to-end. This role is for someone with genuine commercial instincts, technical curiosity, and the hunger to grow into a full-cycle enterprise seller. What You'll Do Enterprise pipeline development - Own outbound prospecting into named enterprise accounts through cold calling, email, LinkedIn, and other creative channels — your goal is to open doors that weren't open before - Build and execute account plans alongside your EAE partners: researching target organizations, mapping stakeholders, identifying champions, and sequencing outreach across multiple buying centers - Lead early-stage discovery calls with engineering leaders, FinOps practitioners, and infrastructure decision-makers — and advance those conversations meaningfully rather than just handing them off - Participate in deal strategy sessions, pipeline reviews, and customer-facing meetings alongside your EAE, contributing context and earning credit as enterprise opportunities progress and close - Track your enterprise activity, pipeline, and account progress meticulously in CRM — your RVP/RSD should be able to look at your accounts at any time and understand exactly where things stand SMB ownership - Manage inbound SMB opportunities end-to-end: respond quickly, run discovery, demonstrate the product, handle objections, negotiate, and close - Build relationships with SMB buyers who may grow into larger accounts over time, treating every deal as a long-term investment in PointFive's reputation Brand and market presence - Represent PointFive at industry conferences, FinOps events, and cloud infrastructure summits — building your network and generating pipeline in the field - Contribute to PointFive's market presence through social selling, LinkedIn engagement, and video outreach — we use LinkedIn video as a core prospecting channel, and you should be comfortable and confident on camera Feedback and collaboration - Share what you're hearing in the field — from prospects, from competitors, from stalled deals — with your RVP/RSD and marketing so we keep improving our messaging and approach - Lean on your teammates: the EAEs and your manager are invested in your growth, and the best people in this role use that resource aggressively Who You Are The skills on a resume matter, but the traits below are what actually predict success in this role. We're looking for people who are wired a certain way — not just credentialed a certain way. Curious: You ask better questions than most. You want to understand how things work — your product, your prospect's business, your industry — and that curiosity drives you to keep learning without being told to. Hungry: You have a chip on your shoulder in the best way. You set a high bar for yourself, put in the work, and don't need external pressure to stay motivated. You know that early-stage, high-growth environments reward people who outwork and out-prepare everyone else. Accountable: When something goes wrong, your first instinct is to figure out what you could have done differently — not to find an excuse. You own your numbers and your pipeline, and you follow through on what you say you'll do. Organized. You can manage multiple accounts, priorities, and workstreams without dropping the ball. Your CRM is clean, your follow-ups happen on time, and nothing falls through the cracks. Coachable: You're confident enough to have a point of view, and self-aware enough to update it. You take feedback well, apply it quickly, and actively seek out ways to get better. A strong communicator: Whether it's a cold call, a discovery conversation, a follow-up email, or a Slack message to your AE partner — you communicate with clarity, precision, and the right tone for the situation. Intellectually sharp: Our buyers are technical. Our product is complex. You can get up to speed quickly, hold a substantive conversation with an infrastructure leader or a FinOps practitioner, and make them feel like they're talking to someone worth their time. Entrepreneurial: You treat your territory like a business. You're proactive, resourceful, and comfortable operating without a perfect playbook. When you see an opportunity, you move on it. What We're Looking For - Bachelor's degree - 1–3 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 - Able to work from the office 3–4 days per week and travel occasionally for conferences and events Nice to have - Exposure to cloud infrastructure, FinOps, DevOps, or AI workload cost management - Active LinkedIn presence or comfort with social selling - Familiarity with enterprise sales methodologies (MEDDIC, SPICED, Challenger, etc.) - Experience selling to engineering, infrastructure, or FinOps personas - For London: experience in EMEA markets; additional European language a plus Equal Opportunity Statement PointFive is proud to be an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We welcome candidates from all backgrounds, experiences, and perspectives to apply.