Sales Director

About the role

The Sales Director will drive the end-to-end sales process with senior living operators — from discovery through signed contract. You'll start where our engine runs fastest: single-community and small-portfolio deals with a documented playbook, short sales cycles, and full pre-sales support behind you. As you master the product and the market, you'll grow into larger portfolio opportunities (5–50 communities) alongside our VP of Growth. Commission is uncapped — the ceiling is yours to set.

What makes this seat different

• A documented playbook, not a blank page - call sequences, discovery scripts, objection handling, and battle cards built from deals we've actually won
• Pre-sales support behind you - a dedicated product expert runs demo depth, proposals, and contract admin, so you focus on relationships and closing
• A proven motion - our current cycle on this segment runs weeks, not quarters, with win rates we'll happily share with you in the interview
• A clear growth path - master the core motion first, then step up to portfoliolevel deals as the team scale

Client engagement

• Engage with senior living professionals via phone, email, video meetings, and in person including industry conferences
• Lead discovery that maps the full buying committee: champion, budget owner, technical gatekeeper, end users
• Understand client needs and position Cubigo's value across departments (engagement, dining, operations, family experience)
• Plan and lead high-impact engagements (demos, module deep-dives, on-sites where it matters)
• Deliver fast, specific follow-through: debriefs, tailored proposals, next steps with dates
• Negotiate and close contracts in collaboration with our legal and finance teams

Pitch meetings

• Lead high-impact meetings and product demos with support from the sales engineer and other Cubigo experts
• Tailor each demo to community type and the stakeholders in the room
• Handle common product and integration questions confidently - and know when to bring in additional support

Administration efforts

• Work the pipeline with discipline: honest close dates, clean stages, notes a colleague could pick up cold
• Keep the CRM (Pipedrive) up to date with contacts and relevant sales activity
• Contribute field insight back into our playbooks, battlecards, and selling collateral in partnership with marketing
• Represent Cubigo at industry conferences (SLIF, ASHA, LeadingAge, NIC) and convert conversations into pipeline

Your profile

Required

• 3–5+ years of sales experience in a software business
• Passion for the senior living industry - experience selling into it is a serious plus
• Strong presence and the ability to interface with senior executives
• Outstanding sales skills: driven, proactive, conscientious, team-oriented, and curious, thrives in a scale-up environment
• Knowledge of the full sales cycle (prospecting through contracting) and the discipline to run several concurrent sales deals

Preferred

• Experience selling to senior living operators or adjacent markets (healthcare, hospitality tech)
• An existing network among operators — conferences should feel like home turf
• 5+ years in software sales
• Business, economics, or finance background

Irrespective of background, the successful candidate will be

• Collaborative — knows how to work with and through others to drive results
• Entrepreneurial, proactive, and productive with the ability to prioritize what needs to be done and gets it done
• Insightful and creative with strong problem-solving skills and an affinity for data-driven decisions
• Articulate and compelling — engaging and concise across executive, technical, and internal audiences
• Energetic, with drive and enthusiasm — a natural relationship-builder and strong networker that others enjoy being around

We are in a fast-paced growth environment backed by new investors and a clear mandate to accelerate. If you enjoy rolling up your sleeves and want your work to directly shape how a company scales, you will create success for the client, yourself, and Cubigo.

Practical

Location: Remote, US

Travel: 20-40% based on mix of clients visits and conferences

Start: September 2026

Why Cubigo?

At Cubigo, we're on a mission to modernize how senior living communities operate. We work fast, we're growing fast, and we empower people who take ownership. You'll be part of a collaborative, high-trust team where execution matters and your work directly impacts our clients and their residents.

We value autonomy, curiosity, and people who build solutions.