Gradual

GTM Strategy, Advisor to CEO

“Jill’s unmatched expertise in sales, community building, partnerships, and ecosystems has been pivotal in shaping our product vision and go-to-market strategy. Her unique insights and strategic connections have unlocked new opportunities and accelerated our growth.” – Jerry Li, CEO & Founder

Gradual is a community platform that centralizes all community experiences, driving product adoption and deeper customer relationships.

Strategic Advisor

Stage 2 Capital

Stage 2 Capital invests in early-stage B2B software companies and sits shoulder-to-shoulder with leadership teams to operationalize sustainable revenue growth. We provide expertise and capital to help companies scale. 

Our LP base of 500+ seasoned GTM executives is matched with the strategic and operational needs of our portfolio companies. We involve our network in 100% of our investments, which often includes joining a portfolio company as an executive, board member, or advisor.

In 2018, I helped raise our $15 million Fund I from LPs at Asana, Atlassian, Box, Gong, HubSpot, Okta, Slack, Salesforce, SAP, ServiceNow, Toast, Twilio, Workday, Snowflake, Zoom, and many others.

$15m Fund I, LP, and Associate Member
$80m Fund II, LP
$150m Fund III, LP

GTM Advisor & LP

Klue

GTM Advisor

Competitive Enablement platform that combines market, competitor, and buyer insights.

Raised $81 million from top VCs including Salesforce Ventures, Tiger Global, Craft, and OMERS Ventures.

Advisor

Folloze

Advisor to the CEO

Enterprise customers include Adobe, Autodesk, DocuSign, Okta, VMware, UiPath, Cisco, and ServiceNow. 

Integration partners feature 6Sense, Demandbase, Marketo, Outreach, Qualified, and Salesforce.

nearbound.com

Assisted in the design, launch, and growth of the Nearbound category at Reveal. In June 2024, Reveal merged with Crossbeam, with the unified focus now on driving Ecosystem-Led Growth.

While outbound interrupts and inbound attracts, nearbound surrounds.

Nearbound is essential because buyer behavior has shifted from the ‘How’ economy to the ‘Who’ economy. Buyers now ask, ‘Who can help me solve X?’ and seek out trusted nodes in their network.

Strategy & Champion

Guild

Advisor to the B2B GTM team.

On a mission to unlock opportunity for America’s workforce. When opportunity is as evenly distributed as talent, everyone benefits. Individuals rise, companies grow, and our economy thrives.

In June 2022, Guild raised a $175 million Series F funding round at a $4.4 billion valuation. The round was led by prominent investors including Bessemer Venture Partners, Cowboy Ventures, Emerson Collective, General Catalyst, GSV, ICONIQ, Redpoint, Workday Ventures, Salesforce Ventures, and Oprah Winfrey.

GTM Advisor

LoopVOC

Voice of the Customer software for B2B SaaS Companies. Advisor to CEO & Founder.

Affinio

Member Board of Directors

Sales for Life

Advisor & Partner

Nudge.ai

Acquired by Affinity, a relationship intelligence platform.

Advisory Board Member & Investor

23 years in B2B SaaS Go-To-Market at Salesforce, Eloqua, HubSpot, Marketo. Customer Obsessed. Partner Obsessed. Living-In-Market. LinkedIn Member #320,966

Majored in Customer. Minored in Go-To-Market. Live in-Market. 

24 years in B2B SaaS. Early employee at Salesforce (first 100), Eloqua (#13), HubSpot Advisor (2014-2016), Marketo (2018).

Love startups, especially category creators.

Born Sales. Bred Marketing. Building Partnerships. 

I spent six years in management consulting, 52 quarters in software sales at Salesforce and Eloqua, six years doing professional speaking, 2018 reporting to the CEO of Marketo (acquired by Adobe for $4.75B), Limited Partner "LP" and GTM Advisor at Stage 2 Capital and GTM Fund. 

I started investing in 2012 and maintain my personal portfolio of investments in sales and marketing technology startups. I also started advising startups in 2012 and joined my first Board of Directors in 2016. Four of the companies I've advised have had successful exits -- HubSpot, Accompany, DataRPM, and PartnerHacker. 

My work keeps me focused on the changing B2B buying environment and what revenue teams need to do to evolve their culture, skills, processes, data, and technology. 

****If you want to connect with me on LinkedIn, don't send a generic invite.****

Jill Rowley

A2 Media

📌 Want to see some of our work? Click the video links below👇🏿
I run A2 Media. We’re a team of 8, and we help busy, lean B2B marketing teams create video content that drives pipeline.
💁🏿‍♂️ Our Website: www.a2media.ca 
📞 Book a chat: https://cal.com/ademolaadelakun/meeting

Reveal

Teaching the world how to do partnerships the right way. Through video and Nearbound.

Head of Video Production

Made Digital

We help online businesses build profitable and engaging brand experiences. 150+ merchants and counting.

www.madedigital.ca

Co-Founder & CEO

Alloy

Launch any integration for your business or customers in minutes with Alloy’s low-code, user-friendly iPaaS.

Partnerships Lead

Affirm

eCommerce Partnerships Lead

Partnerships Manager, Canada (PayBright)

Vagabond Cookies

Large, gourmet cookies delivered to your door once a month.

Co-Founder

Shopify

• Guided enterprise merchants ($350M+ GMV) on D2C best practices, industry trends, API & ERP support and social commerce strategies.
• Spearheaded the Merchant Industry Insights Project: built CS team’s credibility with merchants by providing high-value commerce content.
• Host of Shopify News: featured on Shopify’s twitter page, Shopify News is an external weekly social media round-up of product updates and company news.

Customer Success Manager

Vidyard

• Maintained a 95% retention rate across 97 active accounts ($500K GMV/account).
• Increased book of business to 500K (40% revenue growth) through upsell opportunities.
• Presented quarterly business reviews to C-level executives, VP’s, and Managers to outline KPI’s and growth plans.

The Art of Delivery

From appearing on CBC’s Dragon’s Den, to interviewing Leon Bridges, to performing magic in front of thousands of people, public speaking has changed my life. It can change yours too.

Public Speaking Consultant

Bedouin

• Recruited and managed Bedouin's sales team, closing $2M in 8 months.
• Worked directly with Bedouin's CEO to define the company's strategy on a monthly basis.
• Organized and facilitated 10 design thinking workshops for clients.
• Owned relationships with client CEO's directly, from conception through execution.

Account Manager

We help b2b SaaS marketers turn their video footage into leads | Founder at A2 Media | Ex-Shopify & Affirm.

📌 Most B2B brands don't lose to better products or services. They lose to better content marketing.

(We've got 1/3 client spots left for this quarter).

Hi, I'm Ademola! I run video strategy at A2 Media. We're an 8-person team that helps B2B SaaS teams turn video into a revenue-driving machine, with less than 2 hours a week from your team.

Here's what that looks like in practice:
→ Your sales team stops explaining the same thing 100x, because the content already did it
→ Your brand starts showing up in the feeds of people you want to close
→ Your pipeline fills with pre-educated prospects who already understand your value
→ Your content directly drives demos and closes deals, not just brand awareness

We don't make content for likes. 

We build systems that create leads, educate buyers, and position your company as the no-brainer choice.

We partner with B2B SaaS companies that have:
✅ $10M+ in Annual Recurring Revenue
✅ A Marketing and Social Team
✅ Camera-ready talent

Things we've done:
→ Okta: Built multiple video series → 20K subs + 1,000s of DevDay signups in months
→ Reveal: Built 4M+ organic impressions in new markets, resulting in acquisition by competitor
→ Nearbound: Reduced sales time to close by 50% with several targeted video series
→ Nice Commerce: 482% subscriber growth + multiple 5-figure deals through video content
→ A2 Media: Tripled inbound leads with audience-first video edutainment strategy

(We're also trusted by brands like, Chili Piper, Close, Openphone, and Sendoso).

Simply put: when you work with us, you won't need to explain your value on a sales call ever again. Your content does the selling.

Ready to turn your video strategy into content that actually drives results? Book a call with me.

www.a2media.ca

📸 Ademola Adelakun, MBET

Things I’ve actually heard on calls as a Black guy in tech:

“You’re so well spoken.”
“You don’t act Black.”
“I don’t see colour.”
“Do you actually talk like this all the time?”
"You're so professional."
“Was it hard growing up in Africa?”
“Is your dad in your life?”
“You like basketball, right?”
“How old are you? Wow, haha. You know what they say, black don’t crack”
”What’s good my brotha?”
“Word up, King”
“You’re one of the good ones.”
“You’re a fan of [insert rapper], right?”

If you’re on a call with someone and you catch yourself trying to confirm preconceived notions you have, please apologize and then hang up. 

Regards,
Your friendly neighbourhood Black guy.

P.S. Black people, what did I miss here that you’ve heard?

Ademola Adelakun, MBET

Our Videos Kick Ass for SaaS | We run your video marketing; you win more customers | 550+ videos created for clients.

It took me 11 years, and 14 attempts to build a great business.

Because sometimes that’s how long it takes.

We’re all obsessed with the idea of becoming an overnight success.

But we don’t put ourselves under that kind of pressure in 99% of other contexts.

As a baby, you didn’t learn to walk overnight.
You don’t learn a new language overnight. 
You don’t heal from heartbreak overnight.
You don’t recover from botching a magic trick in front of 3.1M people on national TV overnight (just me?)

So why do we expect to build the perfect business overnight?

Here’s what my journey actually looked like:

2014: Dreamed of being an entrepreneur.
2015: Pitched on Dragons’ Den Canada (got rekt).
2016: Got my Masters in Entrepreneurship.
2016: Realized I didn’t know anything about business → went corporate.
2020: Realized most businesses don’t know anything about business.
2020: 9 failed side hustles.
2020: First semi-successful one.
2021: Second semi-successful one.
2022: Burned out → quit everything → hauled ass/ran away to Mexico.
2023: Tried corporate again → remembered it sucks → quit in 4 months.
2023: Started a new business → Signed my first client → Became a full-time contractor.
2024: Signed more clients.
2025: Built a lifestyle business that lets me actually enjoy my life.

Took a minute, huh?

It makes me sad to see brilliant people give up on their ideas because they feel like it’s “taking too long.”

If you knew you were weeks away from a breakthrough that changed everything, would you keep going?

Probably.

So operate like you are.

Stay open-minded.
Talk to the right people.
Test things fast.

And don’t quit just because your timeline isn’t working out. 

Because it never does.

I’m excited to announce that I unknowingly am the engineer behind seamless payments millions rely on EVERY year. 

P.S. If you think we look alike, yes, you’re racist.

No alternative text description for this image

is anyone else's wrapped like, wayyyy too accurate??? 😅

A2 Media Wrapped (2025)

This is my latest masterpiece. 

No editing needed. For two reasons:

1. The subject Maggie Arai is stunning.
2. The sunset is also stunning.

In that order.

If you’re not following Maggie or that sunset on LinkedIn already, you’re missing out on peak vibes.

Why?

Just trust me bro.

📍Bangkok, Thailand.

P.S. I’m writing this post while on the back of a motorcycle to prove that I’m a local now (proof in the comments).

Today, I realized my old profile picture didn’t do A2 Media justice.

That’s why I spent $14.7M on a brand refresh.

I’m so excited to introduce: “i see u”

A profile picture that visually represents the watchful eye A2 Media keeps over all of your video marketing operations when we work with you. 

P.S. We’re now looking to raise a $14.8M round. My DM's are open.

In 2020, I started learning Japanese with one goal in mind.

Pull the world’s most epic prank on my friends. 

My plan was flawless: 

Step 1: Learn Japanese in secret for 1 year. 
Step 2: Host a big birthday party/gathering. 
Step 3: Fake a dramatic tumble and hit my head.
Step 4: Wake up “forgetting English” and only speaking fluent Japanese.

So I got to studying.

One week became a month.

A month became six months.

A year passed, and I still couldn’t speak Japanese even a little 😂

At that point, I gave up on learning in secret and decided to learn in public instead.

(That’s how I keep myself accountable. Tell as many people as possible about my goals).

Four years in, I finally felt comfortable speaking Japanese, joking, teasing, messing around… the way I do in English.

And once I realized I could finally express myself the way I wanted in Japanese, I chose a new goal…

Mess with as many Japanese teachers as possible. 

With card magic of course. Nothing crazy.

I mean, it’s only fair right? 

I couldn’t mess with my friends in 2020. Someone has to pay.

Learning Japanese has been one of the most humbling journeys of my life.

And there will always be things I need to learn.

That said, if I’m going to keep going, I might as well have fun with it - right?

Enjoy the video :). 

P.S. If you speak Japanese, DM me! Would love to chat with you 😁

My Fiancée (Maggie) is kicking me out of the house.

And the reason is pretty stupid if you ask me.

Picture this:
You've just had an amazing breakfast.
You're co-working at the same table as the love of your life.
The sun is shining.

And then *boom* you get a calendar invite.

All it says is, "Mastermind dinner."

And you think to yourself, "Omg, is this a date night where we talk about our business goals for 2026?" 😍

“What should I wear to this? I’m so excited!” 

Just as your heart is swelling with excitement she looks at you and says...

Her: “Did you get my invite?”

Me: “Yes, my love - I did! Where do you want to go to chat about our goals?”

Her: 😬

Me: “What’s up?”

Her: “Actually, this is a dinner I’m hosting for the ‘Founders who give a F*ck’ group. Are you able to find something else to do that evening?”

Welp.

So, the thing is… I’M not allowed to go. 

But if you’re reading this - there’s a chance that you're allowed to.

This is an exclusive group for founders that:
1. Have a mission-driven business (think: making people's lives better)
2. Believe in collaboration over competition
3. Know the best way to grow is with support and community 

It’s happening on December 17th, at MY HOUSE at 6:30pm.

Will someone let me know how it was?

I will be at Chipotle.

📌 Link here: https://lnkd.in/gqtncNBm

P.S. Even if you don't live in Toronto, apply for future versions. They'll be online, and I STILL won't be invited to those apparently.

I just learned a new magic trick. Thoughts?

Jokes aside, A2 Media’s tech stack and offer is about to be insane.

So what does that mean for our clients?

We’ve spent years mastering visual storytelling, editing, and all the invisible things that actually make viewers pay attention and learn to trust you.

Now combine that with AI tools that help us lean into those strengths and create more efficiently?

Things are about to get really interesting.

If you're looking to hit the ground running with video content that not only looks amazing, but actually wins customers, you're going to want to work with a team that’s done this many, many times before.

You need to make videos that position your brand as the obvious choice. 

Work with us 👉🏿 https://www.a2media.ca/

We’ve had a massive surge in inquiries this quarter, and we won’t be able to take everyone on. We’ll be choosing best-fit partners over the next couple of weeks.

P.S. Want to see our clients and results? Link in bio.

If you want to 493x your leads INSTANTLY, start shitposting.

I’m half-joking, but we’ve had a big surge in inquiries recently.

Many of which came in while I’ve been on vacation posting about:

→ Being terrorized by a symphony of farts on a 14-hour flight to Hong Kong.
→ Spending $14.7M on an awful rebrand (peep my profile photo).
→ Announcing that I’m quitting A2 Media to live in the forest amongst elephants.

Is everyone ok?

On a serious note: We’ve now got twice as many inquiries as we’re able to take on through the first quarter of 2026.

So I thought to myself, why not make it THREE TIMES AS MANY? 😈

….

Over the next couple of weeks, we’ll be choosing the best-fit partners to work with. 

The ones who want to experiment, test fast, build momentum, and are genuinely ready for a serious video engine.

We’re not for people who want one-off videos, are chasing virality, or think AI-generated can fully replace a real content strategy.

But if you’ve ever caught yourself thinking:

→" People still don’t ‘get’ what we do.”
→ “Our content should be driving way more pipeline than it is.”
→ “We don’t have the time or team to do this properly.”

Or if you’ve ever wished buyers would show up already sold because your content did the heavy lifting...

Then this is for you.

What you're likely missing is a video strategy rooted in customer research, and a team that can run it and evolve it for you, consistently.

That's what we do.

👉🏿 Work with us: www.a2media.ca

P.S. Want to see some of our enterprise clients and results? Link in bio.

P.P.S. Shitposting is not actually a strategy. But showing you have more than one dimension as a brand *is*.

The last 5 weeks have been unreal.

From chilling in Hong Kong, to spending time with half of my insanely talented team in Cebu, to hanging out in my favourite city in the world, Bangkok, and even attending one of my best friend's weddings while I was there.

I couldn't have asked for a better reset. 

However, going from paradise and perfect weather to SNOW AND FREEZING TEMPERATURES IN CANADA HAS BEEN HARROWING.

WHY DOES ANYBODY LIVE HERE? EXPLAIN IT TO ME.

Anyways, Bangkok, I'll see you again in April :).

And who knows, we just might end up staying there long term 😉.

P.S. I need all of you to help me convince our families to move there. Petition coming soon.

Last week, I spent $14.7M on a company rebrand.

This week, I’m quitting A2 Media to live amongst elephants in Thailand.

Jude, Patricio, if you’re reading this - split the company 50/50.

My lawyers will be in touch.

If you have questions and you need to contact me, don’t.

I’m one with the forest now.

Passive-aggressive comms are what I hated most about corporate.

So I don’t tolerate them anymore.

Most issues take a few minutes to resolve.

They only drag on when people avoid being direct.

I’ve found that this one question either clears the air instantly, or reveals exactly the kind of person you’re dealing with.

Other bangers🔥 🚀🧨:	
“Are you having a bad day?”
“Do people normally let you talk to them like this?”
“I hate you”

(Okay, I don’t actually use those last two because they’re not productive 😂)

All I’m saying is, be direct, and be helpful where you can. 

But if you’re being an unhelpful jerk because you're having a bad day...

Be better.

Running away from my problems in Canada, part 2.

I finally got to meet part of my team in the Philippines! 

And somehow they’re even cooler in person.

Of my 5 weeks in Asia, the three days we spent together were among the most memorable.

We all flew to Cebu, grabbed a beautiful villa-like Airbnb, and just… vibed.

Sun, food, stories, dancing, laughs. The good life.

I mean, look at how much fun we had together 😌

Your team is one of the most important, if not THE most important decision you’ll make for your business.

If you can find insanely talented people who are also genuinely good human beings, you’ll build things that you didn’t think were possible. 

We wouldn’t be anywhere without you guys, and I’m very grateful and blessed to have you. 

I miss you guys already. 

Let’s make 2026 our best year yet. 

P.S. Patricio Londaits, Jude A. Alonso, and Noel, you’ll be at our next retreat, yeah? 😁

You don’t know suffering until you’re one minute into a deep-tissue massage and realize you have to hold in a category-5 fart for 59 more minutes.

LinkedIn: "We want to see more thought leadership videos."

Me: *Makes fart jokes*

PSA: Take a sec to slow down please. Do you like sunsets?

Cool. Take a sec to watch one with us, then go about your day :).

The point of a sales video isn’t to hype up your company.

It’s to change what your viewers believe. 

We all know hard selling rarely works.

And most teams are STILL hard-selling in their content… they just think that they're slick 😂

But c'mon, we both know that your viewers are smarter than that 😅

Sales videos that actually convert do these four things exceptionally well:

1️⃣ They speak to one person.

Not everyone, just your best-fit buyer. You’ve done enough research to talk directly to that person’s current reality. That’s the kind of magic that makes viewers say things like “This video is literally me lol” and then proceed to watch the whole thing. 

People love when things feel personalized, and when they come at exactly the moment they needed to hear it.

2️⃣ They meet your viewers exactly where they’re at now.

Their frustrations. Their confusion. The beliefs they’re holding today. The best sales videos start their scripts there. By showing your viewer that you understand them, and that you (or your customers) have been in their exact shoes, you build trust that you can actually solve their problems.

3️⃣ They break the misconceptions that keep people stuck.

Buyers need to see what happens when bad-fit paths are explored too. The tactics that flopped, the assumptions that weren’t true, the detours that wasted time. 

When you share the false beliefs you held (or your customers held) and how acting on them actually made things worse, the viewer feels their own beliefs start to crack. And once that happens, there's room for new beliefs in their mind.

4️⃣ They show what helped you and your customers change everything.

Once their old beliefs have shattered, you can show them a new path forward. A future your buyer actually wants. When people see their own story reflected throughout the entire journey of your sales video, they don’t feel hard sold, they feel understood. Then they realize something needs to change.... And that’s where you come in, my friend 😉.

There’s a name for this structure. It's called "The Epiphany Bridge 💡"

We implemented this about a month ago, and the results have been insane.

Our current hero sales video has a conversion rate of 30%.

So I’m sharing our full Video Sales Letter breakdown with you.

Because all of us deserve a sales video that actually sells, right?

Here's how you get it: 

→ Step 1: Tell me one thing you love about me in the comments. I'm a words-of-affirmation kinda guy.
→ Step 2: DM me. My auto-responder will send you the breakdown instantly. 

‼️ DM me before Saturday, December 13th. After that, the link disappears (My auto-responder only gives me 300 characters and I need that real estate for other things 😂).

Word of caution: Use this wisely. This is powerful stuff.

Are most Black Friday/Cyber Monday (BFCM) deals a scam?

If you don't think so, prove it: 

Link the most insane deal you’ve found this month in the comments👇🏿

Anything goes! Gadgets, subscriptions, kazoos. IDGAF. 

Let's all help each other out. 

This is all because I have a terrible habit of missing good deals, regretting it for a year, and then missing them again 😂.

NO MORE. 

I’ll start. A friend of mine told me about a ridiculous deal from Higgsfield AI. If you’ve been curious about AI video and you want to hit the ground running, try it out. It aggregates all of the best video AI tools currently out there. 

(This is not sponsored lol).

Link for the Higgsfield deal in the comments. 

P.S. If you’re the one running a BFCM deal, plug yourself below. 

P.P.S. I bet you're wondering who designed this graphic? It was me. I'm available for hire. Book me before my rates go up in 2026.

taplio

The Battle

Jill Rowley

📸 Ademola Adelakun, MBET

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taplio

The Battle

Jill Rowley

📸 Ademola Adelakun, MBET

Followers

Posts

Engagements

Likes

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);}📸 Ademola Adelakun, MBET's LinkedIn Performance

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