Scale operator Jobs in Saskatoon, SK

About AI Acquisition

AI Acquisition is a bootstrapped, multi-entity business helping founders and operators scale with AI. We combine SaaS platforms, consulting, and a full sales and delivery engine. We manage thousands of active clients across multiple products and operate globally.

The Role

You're taking over an existing book of established client relationships. These are not new clients figuring out what they bought. They've been with us, they know the product, and they have expectations built on months of experience with the business.

Your job is to keep them progressing, keep them retained, and keep them expanding. That means understanding where each client actually is in their business, what's working, what's stuck, and what they need next. Not checking in for the sake of it. Actually moving the needle on their results.

This is a consulting role disguised as account management. You're not managing a spreadsheet of renewals. You're advising business owners on how to grow: how to frame their offer, how to think about their funnel, how to close deals, how to handle fulfillment, and how to use AI to do all of it faster.

The clients you inherit will have history, context, and in some cases, frustrations that predate you. Your first job is to audit that book, understand every account's real status, and earn trust through competence rather than promises.

Requirements

What You'll Own

• An established portfolio of legacy clients across various stages of maturity and engagement
• Regular check-ins, growth workshops, and strategic conversations with business owners who are building and scaling real companies
• Client retention — spotting risk before it becomes a refund conversation, re-engaging clients who've gone quiet, and resolving issues without escalation
• Business consulting — advising clients on offer framing, lead generation strategy, sales process, prospecting, closing, and fulfillment. You need to understand these well enough to coach, not just relay information
• Upsell identification — knowing when a client is ready for more and positioning the next step as the natural move, not a sales pitch
• Cross-functional coordination with the onboarding, deliverables, and office hours teams to make sure nothing falls through the cracks
• Documentation — every interaction, decision, and next step logged so anyone picking up your account knows exactly where things stand

What We Need From You

• Native or near-native English fluency is non-negotiable. You will be on camera with clients daily and every conversation needs to land with clarity and confidence
• Direct experience as a CSM, account manager, or business consultant where you personally advised clients on how to start, grow, or scale a business. Not just managed the relationship, actually consulted on the business itself
• You understand the mechanics of lead generation, sales funnels, cold email, LinkedIn outreach, and how they connect to a client's revenue. You don't need to execute campaigns yourself but you need to diagnose why one isn't converting and coach the client through it
• You've managed a portfolio of clients where retention and expansion were your responsibility, not someone else's
• You're comfortable with difficult conversations. Clients who are frustrated, clients who are stuck, clients who need honest feedback about their own execution. You handle these with composure and directness
• You come with solutions, not just problems. When something breaks in a client's journey, your instinct is to propose the fix, not report the issue and wait
• You pick things up fast. The biggest challenge for external hires in this role has been the knowledge gap — there is a lot to learn about our products, processes, and client journeys, and you need to absorb it quickly enough to be credible in front of clients within weeks, not months
• You're comfortable with AI tools and either already use them in your work or will learn without being told to
  

This Is Not For You If

• You only know relationship management without the business consulting layer. "Keeping clients happy" is not the job. Moving their business forward is
• You need months to ramp before you can have a real conversation with a client. Our clients won't wait that long
• You're uncomfortable advising business owners on sales, prospecting, or offer strategy. That's a core part of the role, not a nice-to-have
• You avoid hard conversations or tell clients what they want to hear instead of what they need to hear
• You wait to be told what's wrong rather than finding it yourself

What Success Looks Like

• Your clients are progressing, not just retained. Business results, not just satisfaction scores
• Clients at risk are flagged and handled before they escalate. You're the person who prevents the refund conversation, not the one having it
• You've audited your book within the first two weeks and can articulate every client's real status, not what's in the notes
• You're coaching clients on their business, not just updating them on deliverables
• You pick up the product knowledge fast enough to be credible in front of clients by week three
• You adopt new tools and processes without being chased

Benefits

The Environment

This is a high-performance, remote-first team at the cutting edge of AI-powered business building.

• Direct access to department heads from day one
• Strong performers progress quickly based on what they deliver, not tenure
• Exposure to AI-led systems and tools daily
• Autonomy and ownership over your portfolio
• A team that holds a high bar and expects the same from everyone

This role operates as an independent contractor engagement: invoice-based, permanent structure, regulated notice periods on both sides. We expect 50 to 60 hours a week from our best people, not as a crunch but as the natural shape of work that matters.

If you're looking for structure handed to you, this isn't the right place. If you want to be the one "Lifting the Hood", build something real, and raise the bar every week with a team that moves fast, we want to talk.