AI Strategist

About Beacon Holdings:

Beacon acquires and grows essential small businesses powering the Real Economy. We are the Berkshire Hathaway of the AI era, and have raised $550M+ to realize our mission.

The Real Economy deserves access to frontier technology and frontier talent. We believe equipping them to compete is a worthy pursuit for our generation’s brightest minds.

About the role:

You will lead AI deployments for the end customers of our portfolio companies, working tightly with our GMs to turn trusted relationships into new AI business. You own the engagement from the first conversation through delivery and expansion: finding the opportunity, aligning stakeholders, defining the solution, scoping and pricing the work, and winning the business.

Alongside AI Engineers, you will lead delivery and stay accountable for the result. That means systems people actually use, measurable value for the customer, and engagements that exceed expectations while staying on budget and on schedule.

Your work also creates opportunities beyond the original customer. When a deployment solves a problem others share, you will work with the GM, product, and engineering teams to turn it into a capability within the portfolio company’s existing product and help bring it to market for the rest of its customers.

This role combines entrepreneurship, product development, sales, and execution. You will go 0-1 and scale repeatedly, with the relationships, technical talent, and resources of Beacon behind you.

In this role, you will:

• Find and win opportunities. Work with our GMs and their customer networks to identify valuable problems, open doors, and build a pipeline of AI engagements.

• Understand the work deeply. Spend a LOT of time with customers. Learn their workflows, inspect their data, and identify where AI can meaningfully improve cost, speed, quality, or revenue.

• Scope, price, and close. Turn discovery into a compelling business case, a concrete solution, and commercial terms that work for both the customer and Beacon.

• Earn trust and work a room. Lead discovery sessions, demos, workshops, and executive conversations. Read the room, find the real decision-makers, build champions, and turn competing priorities into a shared plan.

• Lead delivery end to end. Partner with AI Engineers to own milestones, budgets, dependencies, and customer communication. Unblock the team, manage scope, and keep commitments.

• Drive adoption and expansion. Stay close after launch, measure results, and make sure users realize the value. Earn the next engagement through the success of the first.

• Turn deployments into products. Recognize when a customer solution has broader demand. Work with portfolio product teams to define what should become a repeatable offering, how it fits the existing product, and how to package, price, and sell it to other customers.

You are a great fit if you:

• Take ownership, move quickly, and create structure without waiting for instructions

• Can work a room, earn trust with frontline users and executives, and ask for the sale

• Think clearly and communicate cogently under pressure and on the fly

• Have strong commercial judgment and care about scope, pricing, margins, and customer ROI

• Can get hands-on with data and AI tools to test an idea and work effectively with engineers

• Have product intuition: you can distinguish a customer-specific requirement from a problem an entire market will pay to solve

• Want to deliver real value to real businesses serving real people

Ideal candidates likely:

• Have been a founder, deployment strategist, FDE, consultant, or technical product leader

• Owned complex customer engagements from the first conversation through delivery

• Built, sold, or scaled something people paid for

• Turned early customer work into a repeatable product or offering

Logistics:

• Education requirement: Doesn’t matter. If you are exceptional, you are exceptional.

• Location policy: Able to work 4 days a week from our office in Toronto.

The Real Economy is waiting for you. Let’s get to work.

Our Values at Beacon Software

• Humility: We acknowledge that the path to getting to the right answer involves being wrong along the way. We have strong beliefs which are weakly held. We actively seek new ideas and believe we can learn from anyone at any time.

• Honesty: We are truth seeking in our approach to business problems. Business is a repeat game and we believe that human relationships generate alpha. We understand that trust is earned over a lifetime and can be lost in an instant.

• Hunger: We play to win. We hold ourselves to high standards and will not be outworked. We take pride in having a deep sense of responsibility to ourselves, each other, our partners, and our customers. We believe to whom much is given much is expected.

• Horizon: We seek to build a generational software company. This will take decades. We manage our expectations and those of our partners to take advantage of the 8th wonder of the world - compounding growth.

How We Use AI in Our Hiring Process: To ensure transparency, we want candidates to know that Beacon Software uses Artificial Intelligence and AI-enabled tools to assist with screening, reviewing, organizing and highlighting profiles and applications that match the key requirements for each role.

AI does not make hiring decisions: Every application is reviewed by a member of our team, and all decisions throughout the process are made by humans. We use AI to support efficiency and consistency, not to replace human judgment. We are committed to a fair, thoughtful, and equitable experience for every candidate.