Inside Sales Representative

PointFive Ltd.; Boston (MA); On-site; USD 70,000 - 125,000; Full time

Benefits offered by this job

Equity

Health, dental, vision

PTO

401K

Meal & commuter benefits

Job summary

PointFive, the AI Efficiency OS, is hiring an Inside Sales Representative to accelerate our enterprise pipeline and manage inbound SMB opportunities end-to-end from the Boston office. This growth seat partners with Enterprise Account Executives to penetrate named enterprise accounts and own inbound SMB opportunities.

You will prospect named enterprise accounts via cold calling, email, LinkedIn, and other channels, build account plans with EAE partners, and lead early-stage discovery calls with

Qualifications

• 1–3 years in a sales or revenue-facing role (SDR/AE/AM/CSM).
• Technically curious; translate technical value to business outcomes for engineering/FinOps buyers.
• Comfortable with cold calling and multi‑channel outbound.
• Strong written communicator; clear emails and follow-ups.
• Familiar with CRM tools (Salesforce, HubSpot) and sales engagement platforms.

Responsibilities

• Own outbound prospecting into named enterprise accounts via cold calling, email, LinkedIn, and other channels.
• Build and execute account plans with EAE partners, researching organizations and sequencing outreach.
• Lead early-stage discovery calls with engineering leaders, FinOps practitioners, and decision-makers.
• Participate in deal strategy sessions, pipeline reviews, and customer meetings with your EAE.
• Manage inbound SMB opportunities end-to-end: discovery, demo, objections, negotiation, and close.

Skills

Cold calling

Multi-channel outreach

Written communication

Commercial instincts

Tools

Salesforce

HubSpot

Job description

PointFive is the AI Efficiency OS. From the cloud to the coding agent, we're the only platform that manages AI spend everywhere it happens.

Engineering and FinOps teams use PointFive to make their organizations more efficient and their cloud and AI more effective. We don't just show what you spend. We show what you're wasting, and we fix it autonomously. NuBank saw ROI in 10 days. Customers average 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.

About the Role

We're hiring an Inside Sales Representative to accelerate our enterprise pipeline and own our inbound SMB business — partnering directly with Enterprise Account Executives to penetrate named enterprise accounts, and owning inbound SMB opportunities end-to-end. 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.

Participate in deal strategy sessions, pipeline reviews, and customer-facing meetings alongside your EAE.

Manage inbound SMB opportunities end-to-end: discovery, demo, objection handling, negotiation, and close.

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

1–3 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 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.

Base Salary Range: $70,000 – $87,500

Competitive OTE range: $100,000 – $125,000 with uncapped commission, plus equity

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.

A clear growth path — this seat is designed to develop into a full‑cycle enterprise seller, working shoulder‑to‑shoulder with EAEs from day one.

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.