Bo Bergstrom 🌎

Game Plan Tech

Driving Innovation
I specialize in driving the successful implementation and integration of cutting-edge artificial intelligence solutions to fuel business growth and innovation. At Game Plan Tech I work at the intersection of strategy, technology, and collaboration, ensuring AI technologies deliver measurable impact for large institutions such as government. If this sounds like something your organization could use, then feel free to reach out.

Key Areas of Focus:
	•	AI Strategy & Deployment: Crafting and executing strategies for integrating artificial intelligence solutions that align with organizational goals, optimize processes, and deliver measurable ROI.
	•	Cross-Functional Leadership: Partnering with stakeholders across all levels to ensure seamless integration of AI technologies into existing systems while fostering innovation and collaboration.
	•	Business Growth through Innovation: Identifying opportunities to leverage AI that solve complex business challenges, drive new efficiency, create new revenue streams, enhance customer experiences, and drive meaningful impact.

Why I’m Passionate About This Role:
The potential of AI to transform industries is already massive and the technology is moving fast.  I thrive on turning that potential into actionable solutions. As an entrepreneur I gained firsthand experience with the challenges leaders face when integrating emerging technologies into their operations. Using that experience in combination with the team’s expertise in AI technologies, I aim to create meaningful change that drives innovation where it’s needed most - in large organizations.

Even more important than the technology is the team of people deploying and supporting it.  Game Plan Tech is a mission-driven consulting and services firm with expertise helping government teams access the technologies that drive innovation. We’re committed to creating impactful solutions that push the boundaries of what’s possible.  In short, it’s a great team.

AI Deployment Strategist

Grenadier Consulting

Artificial intelligence (AI) is revolutionizing industries, and Grenadier is at the forefront of this transformation. Our team of experienced AI consultants combines deep technical knowledge with a keen understanding of business strategy to deliver tailored solutions that drive innovation and growth.

Our Services:

AI Strategy and Roadmap: We help clients develop a comprehensive AI strategy aligned with their business goals. We identify key use cases, evaluate investments, and create a roadmap for implementation.

AI Product Development: We assist clients in conceiving, developing, and launching AI-powered products and services. From ideation to market launch, we provide end-to-end support for successful outcomes.

AI Integration and Implementation: We guide clients in seamlessly integrating AI technologies into their existing systems and processes, ensuring maximum value from their AI investments.

Principal

Protocol Labs

At Protocol Labs, I had the unique opportunity to serve as an Entrepreneur in Residence, where I led the creation of Mosaia, a platform transforming enterprise services through AI and Web3 technologies. My role was to identify challenges in the digital business landscape and develop innovative solutions, aligning with Protocol Labs’ mission to enhance human existence through technology.

Mosaia: Redefining Enterprise Services
Mosaia was created to streamline enterprise service procurement, historically a complex and time-consuming process. By leveraging Large Language Models (LLMs), Mosaia simplifies and automates the process, building decentralized micro-marketplaces that connect Web3 builders with verified service providers, all within a trusted environment.

Key Achievements:

	•	AI-Powered Marketplace: Developed Mosaia’s AI-driven platform, enhancing connections between service providers and Web3 innovators.
	•	Decentralized Trust: Created a marketplace emphasizing trust and efficiency.
	•	Mosaia AI Assistant: Introduced an AI tool for streamlined project management, from briefs to vendor selection.

Advancing Decentralized Marketplaces at Protocol Labs
In addition to Mosaia, I contributed to Protocol Labs’ Web3 marketplace initiative. This platform empowers users with control over their data and interactions, fostering a decentralized ecosystem where builders, innovators, and service providers thrive.

Key Contributions:

	•	User-Centric Ownership: Designed a platform ensuring user ownership and control.
	•	Bilateral Reputation System: Architected a review system promoting accountability for both service seekers and providers.
	•	Data Portability: Enabled users to control their data, ensuring flexibility within the platform.

At Protocol Labs, I focused on creating innovative solutions that intersect AI and Web3, paving the way for a future where enterprise service procurement is efficient, trustworthy, and decentralized.

Entrepreneur in Residence / Marketplace Startup Operator

Bo Insights

Helping companies launch and grow new software products by consulting on go to market strategy (GTM), product-market fit (PMF), post-sale software implementation, and user adoption.

Healthtech Startup | 2021 – 2022
I led research, ideation, user interviews, website design, contracting, and onboarding for the creation of a Decentralized Autonomous Organization (DAO). Due to the non-technical nature of the user base I abstracted away the complexity to convey the importance of incentive alignment in an effort to disrupt and democratize behavioral healthcare services. This successfully drove community engagement and resulted in over 200 member applications in the first 30 days of soft-launch with no budget.

Freelance Consultant

Internal Revenue Service

I managed a portfolio of commercial off-the-shelf (COTS) products that were integral to a large-scale digital transformation program to enhance the taxpayer experience. My responsibilities included overseeing new implementations, ensuring that each deployment was on time, within scope, and fully aligned with the business objectives outlined in the project charter.

As a trusted advisor to the Wage and Investment division, which consists of over 37,000 employees, I was deeply involved in executive stakeholder management, developing detailed project plans, scheduling and coordinating multiple workstreams, tracking milestones, and providing status reports to senior leadership. My role required leading complex, multi-disciplinary projects that involved assessing organizational readiness, creating efficient workflows, and drafting solution design documents that clearly defined the project scope and goals.

One of the most significant projects under my leadership was the congressionally mandated launch of the Central Authorization File (CAF) cloud transformation. This project was a high-stakes initiative that went live in under three months, ultimately resulting in 500,000 submissions within the first year. Building on this success, I then led the expansion of the CAF system from 3 to 10 campuses nationwide, greatly enhancing its reach and operational effectiveness.

Another critical assignment involved taking over the Error Resolution System (ERS) installation, which had fallen three months behind schedule. Through proactive stakeholder engagement, identifying key decision-makers, and removing project blockers, I was able to establish a new schedule that brought the project back on track.

These experiences provided a deep understanding of senior stakeholder management, large-scale software implementations, chatbot design, cloud computing, and the broader challenges associated with digital transformation at a massive scale within a highly regulated environment.

Product Implementation Manager

Humanly

Mental health and wellness startup offering real estate as a service.

I spearheaded a dramatic turnaround for the company, moving it from the brink of insolvency and missed payroll to the verge of profitability within just 18 months. This transformation was achieved through a combination of strategic leadership, rigorous operational improvements, and a relentless focus on growth and efficiency.

One of my key initiatives was overseeing all aspects of employee and contractor hiring, personally scaling the organization’s headcount from a lean team of 2 to a robust and dynamic workforce of 19. This expansion was critical to supporting our growing customer base and ensuring the quality and consistency of our services across all locations.

During this period, we placed a strong emphasis on optimizing our existing locations, standardizing procedures, and refining our opening processes, which resulted in a 10x increase in top-line revenue. Our focus on improving the customer experience was paramount; we developed an automated marketing funnel that not only enhanced customer satisfaction but also created a powerful, scalable word-of-mouth sales engine. This strategy led to a remarkable 400% growth in sold but unopened locations, setting the stage for continued expansion.

All of this progress occurred in the midst of the Covid-19 pandemic, which presented significant challenges to our business model. Despite these hurdles, we successfully renegotiated vendor contracts to reduce costs, raised a crucial bridge round to maintain liquidity, and continued closing new sales, even in a climate of economic uncertainty. Fundraising during this period required proactive and transparent communication with investors, as well as the ability to make difficult, yet necessary, decisions to steer the company through turbulent times. Our ability to adapt, innovate, and persevere during these challenges laid the foundation for sustained success and positioned the company for future growth.

Chief Executive Officer (CEO)

SonderMind

SonderMind: Transforming Mental Healthcare Through a Digital Marketplace

In the competitive healthtech arena, SonderMind emerged as a trailblazer, reshaping mental healthcare from the heart of the Greater Denver Area. Our goal? Address the systemic inefficiencies that plague mental health services.

Revolutionizing Mental Healthcare Delivery
SonderMind's vision was clear: leverage the marketplace startup model to connect therapists and patients seamlessly. By building a two-sided marketplace, we aimed to break down traditional barriers, making mental healthcare access as streamlined as e-commerce.

The Growth Trajectory
From its inception, I was entrusted with guiding SonderMind from a nascent idea to a robust platform boasting a 5 MM run rate. Our growth strategy was multifaceted: meticulous product development, an agile operational roadmap, and fostering collaboration across diverse internal teams.

Operational Mastery in Healthtech
As SonderMind's footprint expanded, my focus shifted towards operational nuances. This involved spearheading key processes, cultivating teams, and mentoring leads. From product innovation to customer support and billing (Revenue Cycle Management or RCM), we grew exponentially. Our dedicated teams, totaling over 25 professionals, served a community of 500+ therapists and catered to the diverse needs of 20,000 clients.

Guided by Data and Goals
In the fast-paced world of marketplace startups, metrics are pivotal. Through rigorous OKRs (Objectives and Key Results), we ensured each team was goal-oriented and adaptive, enabling SonderMind to stay at the forefront of mental healthcare innovation.

SonderMind's Legacy
Marrying healthtech innovation with the crucial domain of mental healthcare, SonderMind stands as a testament to what's achievable when technology meets compassion.

Head of Product and Operations to Chief Experience Officer (CXO)

Uvize

A SaaS Startup's Evolution: From Innovation to Enterprise Success

SaaS startups often lie at the intersection of innovation and enterprise demand. Backed by renowned investors like Techstars and the Foundry Group Angel Syndicate, our company embarked on a journey to carve out a unique space in this competitive sector.

Guiding a Diverse Team
At our core was a team of engineers, designers, SDRs, and account executives. As the lead for sales operations, product, and support, I wore multiple hats, ensuring that our software solution resonated with clients while also overseeing the team's daily operations.

Meeting Real-World Scalability
Our engagement with over 30 universities, notably a 10K student SUNY campus, showcased our platform's adaptability. These implementations were more than just software rollouts; they required understanding each institution's specific needs and ensuring our solutions aligned.

Refining Sales and Market Strategy
Enterprise sales in the SaaS realm go beyond pitching software features. Our Go-to-Market strategies were tailored to address institutional needs, ensuring our pitches and demos resonated. Furthermore, pinpointing the right product-market-fit was crucial. My role often involved delving into various business areas, leading to strategic shifts in our target market and pricing, which subsequently fueled our year-over-year revenue growth.

Valuable Experience
Our startup's growth journey underscores the importance of agility in the SaaS sector. For SaaS companies looking to succeed, it's vital to balance software innovation with strategic market positioning while also realizing that early-stage SaaS sales is one of the truest implementations of Boyd’s OODA loop.  The goal is to iterate as fast as possible to find product-market-fit in a vertical you can scale into.  That is no small task, especially while fighting against very limited runway.

VP of Product and Operations

Northwood Investment Partners LLC

Regional sales representative for a registered investment advisor managing accounts with a value oriented strategy.  We use our financial and operational expertise to identify undervalued companies and special situations to invest in utilizing equities, options and above average cash balances in a concentrated portfolio that offers an asymmetric risk/reward profile.

I developed marketing strategy, sales operations and branding/messaging.

Regional Associate

Occipital

Pioneering the Future of Computer Vision: A Business Development Odyssey

In the rapidly evolving landscape of technology startups, it's the blend of cutting-edge innovation and astute business acumen that sets industry leaders apart. Our venture, backed by the formidable Foundry Group during its Series A funding round, is an embodiment of this synergy. Positioned at the vanguard of computer vision, our company sought to bridge the realms of mobile software and hardware, crafting products that would redefine user interactions in the digital age.

The 0 to 1 Leap
Rooted in extensive market research, our vision materialized into a tangible physical product, evidenced by our successful Kickstarter campaign that garnered $1.3 MM in a month. This wasn't just about a product but a testament to a well-executed business development strategy that resonated with our target audience.  Credit to Adam for his media connections and Jeff for extremely high production standards.

Operational Excellence & Team Growth
Transitioning from Series A to Series B brought operational challenges and opportunities. As our revenue surged 10x and the team expanded 4x, a meticulous hiring process was crucial. Every interview was an exercise in ensuring a match with our startup culture, emphasizing adaptability and passion for computer vision.

Streamlining Hardware Operations
Our journey also involved mastering the supply chain and distribution logistics for our B2C hardware offering. This operational challenge meant optimizing everything from production lines to support systems, ensuring our product reached users seamlessly.

Forging Sales Pathways
Despite being a newcomer without strong brand recognition, our strategic approach to channel partner sales paid off, yielding contracts exceeding $5 MM. This was my primary focus and showed the undeniable innovation and value our product brought to the table.

Director Of Business Operations

I help companies identify, launch, and scale new products.  While the technology itself plays a big role in any new product, I focus on the human factors as much as the technology.

In my previous and current roles, I've taken products and even whole companies from nothing to 2 to 5 million in ARR four separate times now.  In some ways I guess you could say my specialty is 0 to 1, go to market (GTM), greenfield opportunities, or new ventures.  Whether it's an early-stage company that needs that kind of growth, a later stage company looking to launch new products, or an incubator/studio, then I am interested in having a conversation.  

I love quotes - in case you haven't noticed - and equate them to concentrated shots of wisdom.  I also write about life lessons, startups, and whatever it is I'm learning about.  I enjoy learning, especially the early part where the learning curve is steep. So I often write a series of 3, 5, or 10 posts about the same topic.  Then, I move on to the next one so if you subscribe, you better love to learn about new topics!

If you remember one thing, know that I believe no matter what obstacle we may face we can overcome it.  That if we work together, then we can make the world a better place.  It may sound trite, but it's a necessary belief when the media around you is yelling that the world is continually ending!

Founder & CEO @ Lever Talent | Host of The Lever Show | Helping leaders develop talent strategies that leverage a tech-empowered future.

You’re capable of more than you could ever imagine.

I started my career impatient, driven, and a little naive. In my mid-20s, I was sprinting up the corporate ladder… and got fired.  

That moment forced me to get honest about what actually changes a team: clarity, standards, and the courage to hold them.

My belief is simple: as AI and automation take more transactions, the human work matters more. Technology multiplies what’s already there (judgment, trust, focus). Software doesn’t change a team. Cadence does.

In 2022, I followed that belief and started Lever Talent. I work with CHROs, CPOs, and HR or L&D leaders to align talent with the business so teams get better because of technology instead of being buried by it. We make it practical:

• Lead with Leverage: a manager cadence that makes expectations real (and conversations easier)
• MVV that sticks: values → rituals → behavior change
• AI, but usable: 30-60-90 change plans that turn pilots into ROI
• People-ops command center: fewer dashboards, better decisions

With technology, our leverage is limitless. Let’s build teams that prove it.

DM me to get in touch.

Drew Fortin

I’ve stopped believing in generic leadership training.

You can’t copy-paste culture and expect alignment.

We kicked off a new program called Lead with Leverage, and it reminded me how rare true leadership alignment actually is.

Some of these leaders have been with the company for 20 years, yet not one has ever been trained on what leadership actually means inside their business.

They’d done all the usual things: 

- Attended a seminar
- Used a learning platform subscription 
- Had a one-off “manager bootcamp.”

But here’s the problem: 

Management training only works when it’s anchored to the business it’s meant to serve.

That’s why at Lever Talent, Inc. , we build leadership programs with companies, not for them, because culture and strategy can’t be outsourced.

Real leadership development has to answer questions that no generic curriculum ever can:

- What behaviors are non-negotiable for leaders here?
- What does “great” leadership look like in this company?
- What are leaders being asked to do differently right now to win?

When those answers are clear, training becomes actionable.

So yes, leadership training matters.

But only when it’s designed to be applied, not just completed.

That’s the difference between checking a box and actually changing how leadership shows up in your business.

Founder & CEO @ Lever Talent | SHRM-SCP | Helping leaders develop talent strategies that leverage a tech-empowered future.

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The best leaders do the same thing the best parents do:

They raise their teams to be independent of them.

It’s easy for leaders to get stuck in the business instead of working on the business, usually because they don’t trust the system you’ve built.

But if you're a leader and involved in everything, you’re the bottleneck.

Great leadership is creating enough clarity that the business can run without you, and that only happens:

- When the mission is clear.
- When the values actually show up in decisions.
- When people know what’s in bounds and what’s out of bounds.

You can only make so many decisions yourself before you hit a ceiling.

The only way to scale is to build a system where others make the same decisions you would, without asking.

And yes, it can feel like working yourself out of a job.

But that’s the point.

If your leadership still requires you everywhere, all the time, you haven’t built a system.

You’ve built dependence.

NVIDIA is one of the most valuable companies in the world.

Jensen Huang proudly says he runs a flat org with 40 direct reports, no 1:1s.

People are idolizing it like it’s the future of management.

But that structure only works in context.

If you’ve built a deeply tenured, insanely high-skill team over decades, maybe you earn the right to that span of control.

That’s the exception, not the operating model most companies can just copy-paste.

We’re heading toward a world where fewer people run much larger organizations. 

That means leaders oversee more, control less, and must trust deeper.

Because the moment your org grows, your job as a leader must evolve too.

Your brain only has so much time and attention. At scale, control becomes an illusion. 

The moment your organization grows, the job of a leader has to change with it.

Great leadership isn’t:

- Knowing everything.
- Approving everything.
- Overseeing every decision.

Great leadership is:

What people do when you’re not there.

Relinquishing control is a skill.

And the sooner leaders learn that, the faster their organizations actually grow.

Culture is the single biggest reason people quit.

And it’s the one thing most leaders still treat like a “soft” topic.

A new survey found that 94% of U.S. workers say workplace culture impacts their decision to stay.

When employees talk about “culture,” they mean things like:

- How connected they feel to their team and the company at large
- How genuine they can be with team members 
- Clarity in roles and responsibilities and alignment to the strategic vision
- Does it feel like everyone is showing up and equally contributing 

Culture isn’t owned by HR. It’s built moment by moment, especially by the people in charge:

- What questions are welcomed (or punished)
- Whether it’s safe to admit you don’t know
- What behaviors get rewarded under pressure
- What happens when you fail or don’t follow through 

And the data says that 22% of professionals plan to leave this year due to values misalignment. Because only 36% believe their company is investing in their growth.

Culture is the infrastructure of a company's success.

How leaders show up, how people are treated, and what’s rewarded under pressure all shape whether employees stay, grow, and give their best.

“Prove AI can’t replace you” might be the most dehumanizing sentence to enter the workplace in decades.

I understand what Shopify’s CEO is trying to push on.

AI should force leaders to question bloated processes and low-leverage work.

But the moment the conversation becomes “prove a human is necessary,” you’ve already reduced people to a cost problem.

That’s not how great work gets done.

AI is incredible at execution, pattern recognition, speed, and scale. It’s terrible at context, judgment, trust, and meaning.

Using AI as a gatekeeper for jobs is fundamentally different from using AI as an accelerator for people.

One creates fear, defensiveness, and employees who spend every review cycle justifying their existence.

The other creates better decisions, sharper thinking, and teams that ask higher-quality questions.

And let’s talk about performance reviews for a second.

If AI becomes part of how employees are evaluated, leaders need to be crystal clear about what they’re optimizing for.

If leaders don’t take responsibility for defining that relationship, employees will fill in the gaps themselves.

And fear always fills the gaps faster than clarity.

AI shouldn’t be about replacing people.

It should be about figuring out how much more people can do when the machine finally carries its share of the load.

The best career advice I ever got?

Follow what makes you forget to check the clock.

Here’s the litmus test I’ve come back to over and over again in my career:

When you’re truly aligned with your work, you lose track of time.

You start thinking, “I should take a break… but I can’t wait to get back to this”.

We’ve all felt it somewhere.

Maybe it was a creative project, or a problem you couldn’t stop thinking about. 

Something that pulled you in so deeply, you forgot the clock existed.

That’s what work feels like when it’s aligned. It fuels you.

So when someone says, “I just want to work my hours and be done,” I get it, we all need balance.

But I also get curious:

Have you immersed yourself enough to see if the spark is there?

Or are you still standing at arm’s length?

And if the answer is honest, “This doesn’t do it for me,” then the next question matters even more:

Where do you lose track of time?

And how might you turn more of that into something valuable?

Your career is the greatest asset you’ll ever own. You get out what you put in.

The worst kind of leadership is the kind that hides bad news behind a smile and calls it optimism.

The kind that insists everything is fine when everyone can see the flames.

This forced positivity is a trust killer; all it does is erode employee confidence and doesn't boost morale. 

Because when leaders only share the upside and deflect hard questions with vague platitudes, all that grows is suspicion.

When words and actions don’t match, people assume the worst.

If your strategy relies on pretending the dumpster fire is just a “temporary heat source,” don’t be surprised when your best people start looking for exits.

Being truthful as a leader doesn’t mean dumping confidential details or catastrophizing the future.

It means being honest enough to say:

“Here’s what’s going well, and here’s what’s not. This is what we’re doing about it. And while I may not be able to share everything, here’s what I can...”

People expect honesty, accountability, and a little humanity from their leaders.

So have the hard conversation. Trust me, your team can handle it.

We spend millions on performance management systems that everyone knows are broken.

I used to think we could fix them with better tech or cleaner rating scales. 

I was wrong.

The issue is these systems weren’t built for actual humans.

The moment you tie feedback to compensation, people go into threat mode. 

- Brains shut down
- Learning stops
- Managers inflate ratings to avoid conflict

And innovation dies quietly in the corner.

Here’s the shift I push leaders to make:

Stop trying to measure people better. Start making better decisions about them.

Ask:

Who created real impact?
Who’s ready for more?
Who actually needs support?

When you separate pay discussions from development, everything gets clearer, and more human.

Performance management isn’t just outdated. 

It’s built on the wrong assumptions about how people work.

Leaders have a choice: keep managing by myth or start leading by design.

Which part of your system needs to go first?

I think I finally found the image that best describes me, trying to keep up with AI learning.

We use AI every day at Lever Talent, Inc. . It’s part of how we work, how we think, how we experiment. We're continuously building it into our client-facing programs and internal processes.

And I’ll be the first to admit: there are moments when I feel behind. Because I should.

AI is moving faster than any leadership shift I’ve seen in my career. The only way I know how to respond is to keep learning constantly.

To read, to test, to break things, and to talk to people who know more than I do.

But what worries me is the leaders who don’t feel continuously overwhelmed.

In most big decisions, reorgs, restructures, and investments, we want ~70% confidence.

But with AI, I’m seeing leaders operate at 50% confidence and call it transformation.

Weak leadership is hoping the tool will save them all, which is just denial.

AI can’t rescue a broken operating model or turn mediocrity into excellence.

It only amplifies what’s already there.

So yes, I’m still learning, and drinking from the fire hose.

The only way to lead through change is by staying agile.

I’d rather be soaked and curious than dry and pretending I’ve got it all figured out.

Big Tech is spending hundreds of billions on AI.

But tech unemployment is climbing...

For years, tech was the safest bet in the labor market. There was high pay, high demand, and major tailwinds.

But that era is over. What we’re watching now is a sorting event.

If your skills are tightly coupled to:

– legacy systems
– outsourced execution
– work that AI can accelerate or replace

You’re feeling the squeeze already.

If your skills help organizations:

– design better operating models
– apply AI to real business problems
– lead humans through uncertainty and change

You’re still in demand.

There's this misconception that most companies are “overstaffed.” That's not true, they're misaligned.

They cut people before they redesign how work gets done.

They invest in AI before they rethink roles, decision rights, and incentives.

They pause hiring instead of building confidence and clarity.

That creates fear, and that fear is the real talent risk heading into 2026.

Tech isn’t dying. But the old tech career bargain is.

If leaders were totally honest about their 5–7 year plan, it would look a whole lot like this:

The future is messy. 

Most leadership teams can describe the destination beautifully. It sounds great out loud.

What’s far less clear is the distance between today and that future, and what actually has to change to get there.

That’s the uncomfortable gap. 

The confusion comes down to three words that sound similar, but mean completely different things:

Mission, vision, and values.

Your mission is the reason why you exist. It doesn’t change just because the market does.

Vision is where you’re going in 5–7 years. It should feel aspirational and also a little scary.

Values are what have to change in how people think, decide, and act to get there.

And those values must evolve.

If your company was built on risk-taking, there will come a point where raw risk-taking is no longer an advantage.

If you never evolve those values, you end up protecting the past instead of building the future.

So if your future plan looks a little chaotic on the wall, that’s actually a good thing.

Just make sure you’re being precise and pragmatic about what has to change in order to get there.

Only 6% of Gen Z want to be a traditional leader.

Because we made leadership look miserable.

- Endless hours
- Inbox anxiety
- Burnout disguised as loyalty.

If that’s what “making it” looks like, who would want the corner office?

But there’s something deeper happening here. We’re living through a quiet revolution in what agency means.

Agency used to mean getting promoted, someone else handing you authority.

Now it means owning your time, your values, and your impact.

That’s why when I started Lever Talent, Inc. I kept coming back to this idea:

We need a Jerry Maguire for the individual.

Because today’s headhunters don’t really work for talent, they work for business. They don’t get paid to build your career; they get paid to fill a seat.

But people are realizing they can take ownership of their own careers, fractional, freelance, hybrid, on their own terms.

They’re building agency into the way they work.

Here’s the twist, though, and it’s one too many leaders and creators are skipping over:

You can choose balance.

But if you want flexibility, you might have to trade speed.

If you want balance, you might have to let go of the myth of “having it all.”

The goal isn’t to have your cake and eat it too.

It’s to know which cake you’re baking, and why.

We’ve been hiring backwards for decades.

Job descriptions shouldn’t define the org; the org should define the jobs.

AI is changing how we organize work.

People are one resource.

Tools and partners are others.

AI is reallocating human energy to where it actually matters, which means the real shift needs to be in organizational design.

Most companies still design orgs around people first:

“I need a payroll person.”
“I need an L&D lead.”
“I need a generalist.”

That model is backwards.

Instead of hiring a payroll manager, companies should design for automated compliance, then decide if that’s a person, a tool, or a partner.

Strategy and org design should define the capabilities you need.

Only then do you decide where humans belong.

If AI keeps accelerating, we can’t rebuild our orgs every few years.

That's why the focus needs to be on designing for adaptability from day one.

Because when AI takes the busywork, org design becomes the real leadership job.

I don’t think the AI + ARR conversation is actually about revenue.

I think it’s about leadership.

ARR (annual recurring revenue) has long been the lifeblood of SaaS. It’s a clean signal of durability, predictability, and product-market fit.

But AI app companies aren’t playing the same game.

Right now, we’re celebrating speed. 

Fast ARR. Fast adoption. Fast valuations. 

And I get why, AI is moving at a pace none of us has seen before. $275B in investment will do that.

But I can already see the bottleneck that's about to happen:

When leaders chase metrics they don’t fully understand, they start optimizing for optics instead of durability.

A lot of AI “ARR” today isn’t recurring in the way leaders assume. 

It’s pilots, credits, usage-based experiments, and early excitement multiplied by 12. 

That may satisfy a board deck, but it creates false confidence inside the organization.

And false confidence leads to bad leadership decisions:

– Overhiring in areas before demand is proven
– Betting culture on momentum instead of value
– Promising stability to teams that don’t yet exist

And no, this isn’t just an AI startup issue.

It’s the same leadership mistake we’ve seen in every major shift; AI is just exposing it faster.

It’s time for leaders to start asking harder questions:

Are we building something people depend on, or just trying to look like we are?

AI won’t be the downfall of companies. Leadership will, if it keeps confusing activity for impact.

Leaders need to be willing to slow down, tell the truth, and build systems: people, tech, and operating models that actually hold.

That’s responsible leadership.

And it’s about to matter a lot more than ARR charts.

Apple had five CEOs before Steve Jobs came back.

So why do we all think of Apple as the iPhone company?

Because leadership doesn’t just run a company, it defines its identity.

Look at the products Apple shipped under each CEO before Jobs returned:

- Apple II
- Lisa
- Macintosh clones
- Newton
- Copland OS

A dozen experiments that look like they came from entirely different companies

They don’t even resemble each other, and that’s the point.

When strategy is unclear, the product becomes unclear.

Each CEO had talent. Each had a vision.

But they created five different operating systems for the same organization.

Everyone inside Apple was forced to run on whatever version happened to be installed at the time.

Then Jobs returns in 1997 and does something simple:

He deletes almost everything, and he aligns teams to a single, coherent future.

And suddenly, the Apple we recognize is born.

Because of a leadership philosophy that unified product, people, and purpose.

If five CEOs can turn Apple into five different companies, ask yourself:

What version of your company are you creating right now?

And is your operating model capable of delivering the future you keep selling?

Most companies don’t have a clear definition of what leadership means, and that's what sets them up for failure.

Every exec deck starts the same:

At Acme Studios, we value...

“Trust.”
“Integrity.”
“Honesty.”

Cool. But can you explain what your values actually do? How do they help your company move toward your vision?

When I ask leaders to explain, I'm usually met with silence.

For a lot of companies, mission, vision, and values are just boxes to check.

Not systems to operate.

And that used to work when managers could rely on metrics, approvals, and oversight to keep things moving.

But AI is already stripping out transactional work.

Middle management is thinning. Leaders now own more people, more decisions, and more ambiguity than ever before.

But frameworks and dashboards can’t solve that.

Leaders can’t OKR their way through ambiguity, or metric their way to judgment.

That's why real leadership needs to build trust systems so people can make sound decisions without constant oversight.

Because good management is what people do when you’re not watching.

That's why your mission needs to reduce drag, and your values need to accelerate decisions.

Because if your leadership model depends on constant oversight…

The only thing it's causing is friction.

AI is forcing every leader into a choice they can’t dodge:

Do you believe your people are fundamentally creative and motivated, or lazy and in need of control?

Your AI strategy has already answered:

When leaders deploy AI to monitor keystrokes, rank “productivity,” we’re telling people exactly what we think of them.

And people respond accordingly.

- Fear replaces initiative.
- Compliance replaces creativity.

Work stops being about contribution and starts being about survival.

AI is reinforcing our dimmest view of humans that people can’t be trusted unless machines watch them.

But we don’t need AI to tighten control.

We need it to free people from the work that dulls their talent.

The real opportunity is using AI to uncover the potential we’ve buried under bureaucracy:

• Redundant approvals
• Performative documentation
• Meetings that exist because the calendar said so

That’s how you get outcomes AI alone will never deliver.

Leaders need to create conditions for people to think freely again.

So be honest with yourself:

What does your AI strategy say you believe about your people?

Leaders who’ve successfully built even one new venture lean into uncertainty. 

Because they’ve learned something most organizations never do: 

That growth is a leadership problem. McKinsey’s latest research confirms it. 

Yes, the economics have changed. 

AI has collapsed timelines, headcount, and cost in ways that would’ve sounded irresponsible five years ago.

But that’s not why some companies win, and others stall.

The difference is leadership maturity.

The strongest leaders do the hard work: 

Designing teams that can actually experiment, and cultures where learning is rewarded instead of quietly punished.

That takes discipline.

And it takes leaders who are willing to say “no” far more often than “yes.”

Venture building fails when leaders treat it like an innovation initiative instead of an operating model shift. 

You can’t bolt this onto a rigid org, a fearful culture, or managers who’ve never been trained to lead ambiguity.

In uncertain times, it’s tempting for leaders to play defense and optimize what already exists.

But history keeps showing us the same thing: the companies willing to build while things feel uncomfortable are the ones that create the next wave of growth.

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Drew Fortin

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The Battle

Bo Bergstrom 🌎

Drew Fortin

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Drew Fortin's LinkedIn Performance

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