Inside Sales Representative

PointFive•Boston, MA

29d•Hybrid

About The Position

PointFive is the AI Efficiency OS, the only platform that manages AI spend everywhere it happens, from the cloud to the coding agent. Engineering and FinOps teams use PointFive to make their organizations more efficient and their cloud and AI more effective. The company's platform not only shows what is being spent but also identifies waste and autonomously fixes it. Customers like NuBank have seen ROI in 10 days, with an average of 1,200%+ ROI and a 4.9 rating on G2. Founded by the team behind IntSights (acquired by Rapid7), PointFive recently closed a $60M Series B led by Accel, with participation from Entrée Capital and Salesforce Ventures. This role is crucial for accelerating enterprise pipeline and owning inbound SMB business, partnering with Enterprise Account Executives to penetrate named enterprise accounts and managing SMB opportunities end-to-end. It's ideal for someone with genuine commercial instincts, technical curiosity, and the drive to become a full-cycle enterprise seller.

Requirements

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 days per week
Able to travel occasionally for conferences and events

Nice To Haves

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

Responsibilities

Develop enterprise pipeline through outbound prospecting into named enterprise accounts via cold calling, email, LinkedIn, and other creative channels.
Build and execute account plans with Enterprise Account Executive (EAE) partners, including researching target organizations, mapping stakeholders, identifying champions, and sequencing outreach.
Lead early-stage discovery calls with engineering leaders, FinOps practitioners, and infrastructure decision-makers, advancing conversations meaningfully.
Participate in deal strategy sessions, pipeline reviews, and customer-facing meetings alongside EAEs.
Track enterprise activity, pipeline, and account progress meticulously in CRM.
Manage inbound SMB opportunities end-to-end, including responding quickly, running discovery, demonstrating the product, handling objections, negotiating, and closing deals.
Build relationships with SMB buyers who may grow into larger accounts.
Represent PointFive at industry conferences, FinOps events, and cloud infrastructure summits to build network and generate pipeline.
Contribute to PointFive's market presence through social selling, LinkedIn engagement, and video outreach.
Share field insights (prospects, competitors, stalled deals) with management and marketing to improve messaging and approach.
Collaborate with teammates, including EAEs and managers, for growth and support.