Inside Sales Representative

PointFive•Boston, MA

31d•$100,000 - $135,000•Hybrid

About The Position

PointFive is the AI Efficiency OS, the only platform that manages AI spend everywhere from the cloud to the coding agent. Engineering and FinOps teams use PointFive to increase efficiency and improve the effectiveness of their cloud and AI. The platform identifies and autonomously fixes wasted spend, with customers like NuBank seeing ROI in 10 days and averaging over 1,200% ROI. Founded by the team behind IntSights (acquired by Rapid7), PointFive has secured $60M in Series B funding from investors including Accel, Entrée Capital, and Salesforce Ventures. This role is for an Inside Sales Representative responsible for accelerating enterprise pipeline and managing inbound SMB business. The position involves partnering with Enterprise Account Executives (EAEs) to penetrate named enterprise accounts and owning SMB opportunities end-to-end. The ideal candidate possesses strong 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 prospecting
Strong written communication skills: clear, concise emails and follow-ups that move conversations 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

Own outbound prospecting into named enterprise accounts through cold calling, email, LinkedIn, and other creative channels to open new doors.
Develop and execute account plans with EAE partners, including 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, advancing conversations meaningfully.
Participate in deal strategy sessions, pipeline reviews, and customer-facing meetings with EAEs, contributing context and earning credit as opportunities progress.
Meticulously track enterprise activity, pipeline, and account progress in CRM.
Manage inbound SMB opportunities end-to-end, including responding quickly, conducting discovery, demonstrating the product, handling objections, negotiating, and closing deals.
Build relationships with SMB buyers who may grow into larger accounts over time.
Represent PointFive at industry conferences, FinOps events, and cloud infrastructure summits to build networks and generate pipeline.
Contribute to PointFive's market presence through social selling, LinkedIn engagement, and video outreach.
Share field insights (prospect feedback, competitor information, stalled deal reasons) with RVP/RSD and marketing teams to improve messaging and approach.
Collaborate with teammates, including EAEs and managers, leveraging them as resources for growth.