Head of Sales

Head of Sales

The Opportunity The senior living industry struggles to understand why 92% of its leads don't convert. Occulytics provides the data and tools to materially improve that conversion rate, helping operators understand their market, pinpoint wasted spend, and drive occupancy.

We are seeking a foundational Head of Sales to build and lead our commercial engine. This is more than a sales role; it's a career-defining opportunity to establish our platform as the new industry standard, building the entire revenue function from the ground up.

You will be the architect of our sales function, operating as a high-impact individual contributor to hunt and close our most important deals. You will simultaneously build the playbook, processes, and GTM strategy that will serve as the foundation for our future sales organization.

Key Responsibilities

Sales Strategy & Execution (Player)

• Spearhead the complete, full-cycle sales process from lead generation and prospecting to complex contract negotiation and close.
• Design and execute creative outreach strategies targeting senior living operators and investors.
• Architect and deliver compelling proposals, presentations, and ROI analyses demonstrating how Occulytics solves the "92% problem."
• Structure and negotiate complex, multi-year subscription agreements, ensuring a smooth handoff to the client success team.

Go-to-Market Development (Builder)

• Partner directly with the CEO to refine market segmentation, ideal customer profiles, pricing, and competitive positioning.
• Create the foundational sales infrastructure: build the playbook, define sales stages, and implement rigorous pipeline management and forecasting in our CRM.
• Act as the "voice of the market," providing structured prospect feedback to the product and leadership teams to guide the roadmap.
• Identify and cultivate high-leverage channel and referral partnerships to accelerate lead generation.

Relationship & Thought Leadership (Evangelist)

• Represent Occulytics at key industry conferences, roundtables, and webinars, establishing our credibility and brand.
• Become a trusted advisor to prospects and clients, maintaining deep knowledge of senior living sales, marketing, and operations trends.

What You Bring (Qualifications)

Required Experience

• 5+ years of experience in B2B sales, business development, or a senior sales/marketing leadership role.
• Proven track record of exceeding quotas and closing new-logo deals in a "hunter" capacity.
• A "builder" mentality: You thrive in ambiguity, love creating structure from scratch, and are eager to build and scale repeatable systems.
• Executive presence: You communicate with a high degree of confidence and credibility, capable of engaging C-suite leaders.
• Data-Driven: You manage your pipeline and forecast with rigor and accuracy (experience with HubSpot, Salesforce, or similar CRM is essential).

Preferred Experience

• Experience within the senior living industry, either in a sales/marketing leadership role at an operator or in a sales role at a technology vendor serving the market.
• A strong, active network of relationships with C-suite and regional leaders in the senior living industry.

Skills & Attributes

• Strategic & Tactical: You can design a 12-month GTM strategy in the morning and cold-call a key prospect list in the afternoon.
• Self-Motivated: You are an entrepreneur at heart, comfortable owning ambitious revenue targets and operating with a high degree of autonomy.
• Curious & Passionate: You have a genuine passion for innovation in senior living and a deep curiosity about data-driven decision-making.

Why You'll Love It Here

• Build from the Ground Up: You won't just run a playbook; you'll write it. This is your chance to build a high-performance sales organization from first principles.
• Direct CEO Partnership: You will report directly to the CEO, serving as a key strategic partner in shaping the company's GTM strategy and future.
• Direct Impact: Your work will be pivotal to Occulytics' success and will visibly shape the future of the senior living industry.
• Define the Category: Join a fast-growing company poised to redefine how senior living communities use data to solve their most expensive problems and drive growth.

Occulytics Inc. is an equal opporunity employer.

Pay: $140,000.00 - $160,000.00 per year

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Flexible spending account
• Health insurance
• Health savings account
• Paid time off
• Relocation assistance
• Vision insurance

Application Question(s):

• Walk us through a pipeline you built from scratch — what channels did you own, what worked, and what did you learn?
• How have you approached selling into a niche or relationship-driven industry where trust matters more than volume?
• What does your ideal sales process look like from first touch to close, and how have you built or refined that process at a previous company?
• We're an early-stage SaaS company in senior living. How would you think about the first 90 days in this role?
• Tell us about a deal you lost. What happened and what would you do differently?
• WIll you require visa sponsorship to work in the United States now or in the future?

Work Location: Hybrid remote in Chicago, IL 60611