Enterprise Sales Development Representative

PointFive · IT, cloud & dev tools

Hybrid, 3 days/week in office: Boston; must live near Boston, MA (3 days a week in the Boston office)

SDR / BDREntry-level friendly$55k–$70k base · $72k–$100k OTE

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It asks for 1+ year of experience. Apply anyway.

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At a glance

What you'd actually do: Cold call and email named enterprise accounts, run first discovery calls with engineering and FinOps leaders, and book meetings for enterprise AEs.

Pay

$55k–$70k base · $72k–$100k OTE

$55k-$70k base, $71.5k-$100k OTE with uncapped commission, plus equity

Where you work

Hybrid, 3 days/week in office: Boston; must live near Boston, MA (3 days a week in the Boston office)

Selling to

enterprise engineering and FinOps teams

How you'd sell

Inbound + outbound

Experience asked

1+ years

Degree

Required

Tools you'll use

Salesforce, HubSpot

Your game plan for this job

0 of 5 done

Most people just hit Apply. Do these first and you show up with someone on the inside.

1
Pick 2–3 people at PointFive
We haven't found reps here yet. Search LinkedIn for "sales development PointFive".
2
Send a short, curious note
Ask about their experience, not for a referral. We write it for you, with the role and what PointFive sells.
3
Have a 15-minute chat
Good questions for this role:
- What does a normal day look like for you?
- How did you land the job? What stood out in your interviews?
- The posting mentions Salesforce, HubSpot. How much of your day is in those tools?
- How is the team doing on quota? What separates the people who hit it?
4
Apply, ideally with a referral
If the chat went well, ask if they'd refer you or point you to the hiring manager. Then apply and let them know so they can flag it.
5
Prep for the role play
SDR interviews almost always end in a mock cold call. Practice with the PointFive cheat sheet and the role-play guide.

Talk to someone at PointFive before you apply

A friendly message to a current rep is the best way to stand out. Ask about their experience, not for a referral.

We haven't confirmed any current SDRs or AEs at PointFive yet. Try LinkedIn search: "sales development" + "PointFive".

Full job description

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 ENT Account Executives — 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: $71,500 – 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.