About the role

You'll own the full sales cycle, focused on mid-market companies, our core customers. New deals typically land at $5K–$30K in annual value with 30–90 day cycles, and you'll also help grow accounts across our full customer base. Your pipeline comes from three places: inbound leads, expansion opportunities from our Customer Success team, and your own outbound prospecting.

You'll run discovery through close and work with Customer Success to grow existing accounts. Many of your buyers will be IT and security leaders evaluating cloud versus on-premise deployment, so you'll be comfortable in technical conversations and procurement processes.

The role is remote, but we get together in person every so often, so we'd prefer candidates near Austin, TX.

What you'll do

Win new business

• Run the full cycle: prospecting, discovery, demo, business case, negotiation and close.
• Get past features in discovery: uncover the business impact for the customer and the event or deadline that drives a decision through true curiosity.
• Multi-thread every deal: engage IT, security, finance and the budget holder, and equip your champion with a written business case they can take to the decision-maker.
• Qualify rigorously and set honest expectations, so the customers you sign stay and grow.
• Protect deal value: trade concessions for commitments such as contract length or agent minimums rather than discounting.
• Guide IT, security and procurement stakeholders through on-premise and hybrid deployments.

Build pipeline and grow accounts

• Work inbound leads and expansion opportunities from Customer Success, and generate your own pipeline through outbound prospecting and marketing-supported campaigns.
• Partner with CSMs on expansion, from upgrades to cross-selling into new departments: build on their handoff notes, treat these opportunities with the same urgency as inbound, and hand the account back cleanly.

Run a disciplined pipeline

• Keep many deals moving at once, with agendas, recaps and prompt follow-up. Keep every deal current in HubSpot (use case, timeline, success criteria, risks and forecast).
• Build a working knowledge of the help desk, ITSM and self-hosted software market, and share what you hear with product and marketing.

Requirements

What you'll bring

• 2–4+ years as a quota-carrying AE closing $5K–$30K deals with 30–90 day cycles.
• A track record of hitting quota that you can walk us through.
• Real examples of the pipeline you created yourself, not only meetings booked for you.
• Examples of deals you won by working several stakeholders and equipping a champion.
• Comfort selling to technical buyers: IT, security, infrastructure and procurement.
• Experience with land-and-expand selling, including cross-selling into new departments, and working closely with Customer Success or Account Management.
• A consultative style built on the customer's problem, its business impact and what's driving their timeline, not feature tours.
• Discipline with CRM, forecasting and a qualification framework such as BANT, SPICED or MEDDPICC.

Nice to have

• Experience selling help desk, ITSM, customer service or other self-hosted / hybrid software.
• Experience with public-sector or regulated buyers.
• Hands-on HubSpot experience.

Benefits

Compensation & benefits

• $200K OTE: $100K base salary plus $100K variable at target.
• Ramp support while you build pipeline: your quota steps up gradually, you earn commission on every deal you close, and monthly activity bonuses tied to goals you set with your manager make up the difference.
• Commission on both New Business and Expansion deals.
• Benefits: health, retirement, PTO and equipment.

Why join Deskpro

We're sharpening our focus on the customers we serve best and investing in our product to serve them even better. You'll join an agile team with a direct line to leadership and real room to shape how we work.

You'll also have a quota built around deals you can actually win. If you sell honestly, like owning your pipeline, and want your work to visibly move the business, we'd like to talk.

About Deskpro

Deskpro helps organizations deliver exceptional customer and employee support with modern help desk software that brings ticketing, automation, self-service, and AI capabilities together in one platform. We help support teams work more efficiently without losing the human element that makes great service possible.

Equal opportunity

Deskpro is an equal opportunity employer. We value diverse perspectives and are committed to building an inclusive team.