Michael Ocean

SellMeThisPen

No more...

👎 CRM update dilemma
👎 Irrelevant & generic coaching & training

SellMeThisPen AI eliminates non-revenue tasks for sellers and helps leaders scale personalized coaching and practice so everyone can focus on what matters most: revenue growth! 

What SellMeThisPen can help you with: 

✨ Automated CRM updates ✨ Real-time and post-call AI coaching ✨ Role-play practice sessions with AI

Founder & CEO

GoWest.ai

Providing strategic insights on new and ongoing initiatives.

Member of the Board of Advisors

Amazon Web Services (AWS)

Entrepreneur In Residence

Antler

Hopin

Online Event Platform - SaaS

80% Inbound | 20% Outbound - Founding Sales Team

- Helped build the initial sales playbook 
- 900k USD closed-won opportunities created.
- Helped scale the company from 40 Mil USD series A to 400 Mil USD series C.
- Worked closely with the marketing, support and sales ops teams to refine the sales development processes.
- Recognized as the "Pacesetter" in the last month of service.

Founding Sales 

Schedulehead

Event Scheduling Automation - SaaS

50% Inbound | 50% Outbound - First Sales Hire

- Built the initial sales playbook.
- Assisted the CEO with overall sales and marketing strategies.
- Closed, onboarded, and trained 48 SMB & Enterprise accounts in the first five months 
- Hired & trained LDRs & SDRs.

Founding Sales

Bunz

Digital Marketing - Social Media

100% Outbound - First Sales Hire

- Created the V1 outbound playbook
- Helped surpass the Q1 goal in the first month
- Brought in GTA-based clients such as Maple, TruLocal, Flexday, Workhaus and York Region Municipality
- Signed an agreement with the first outside of province client MissFresh

PayamBox

Mobile Marketing - Enterprise Software

*Iteration from M-Theory to an enterprise software solution for the Telecom industry. 

- Raised 400k seed capital 
- Implemented the solution for MTN - one of the largest operators in MENA 
- Worked closely with the technical team for two fully operational products - MBOX mobile marketing SaaS and Telegram MusicBoxBot.

Co-Founder & CEO

M-Theory

Content Production | Mobile Marketing - Telecom VAS 

*Pivoted to PayamBox.

- Helped sign a partnership with "MCI" the largest operator in the middle east
- Acquired 200k+ subscribers - Resulted in $1.2 mil USD revenue.
- Reduced the operation costs by 50% - Built an in-house video production team
- Grew the team to 10

Co-Founder

PCM: The Right Technology, Delivered.

Direct Marketing - Microsoft Cloud

100% Outbound - First batch of Microsoft licensing specialists 

- Surpassed the monthly closed deals KPI month after month
- Helped position the company as the new Microsoft Gold Partner to clients

Account Executive

Two things bugged me the most when I was a sales rep!

👎 Receiving irrelevant & generic coaching & training
👎 Feeling out the CRM 

That's why I am building SellMeThisPen AI to eliminate non-revenue tasks for sellers and help leaders scale personalized coaching and practice so everyone can focus on what matters most: revenue growth! 

What SellMeThisPen can help you with: 

✨Role-play practice sessions with AI ✨Real-time and post-call AI coaching ✨Automated CRM updates

🤝 Feel free to reach out if you would like to chat.

Everyone in the space is obsessed with efficiency BUT blind to what’s coming.


What happens when AI makes your whole sales org faster…but forgettable?

On the SellMeThisPen AI Podcast, I sat down with Kelly Wright, Founder & CEO of Culture Driven Sales, former President & COO at Gong, and the sales exec who took Tableau from $0 to $850M in revenue.


"People buy from people. Companies don't buy from companies."

That’s not fluff, it’s the hard truth about what separates top sellers from the rest.

Kelly built Culture Driven Sales after watching tech companies chase speed at all costs.

Every dashboard. Every pipeline review. Every tool, all aimed at efficiency. 
But as she puts it, AI is going to make everyone equally efficient.

Same data. 
Same speed. 
Same playbooks.

So what’s left?
Your people!


At Tableau, Kelly broadened reps’ development path with storytelling training. Every rep went through it, learning how to connect emotionally, not just close logically.

Within months, customers were calling her asking, “Why are your reps so different? They actually get me.”

That’s what happens when you lead with culture.


Here’s the 3-step playbook she shared to build that edge:

👉 Start with purpose.
If your team can’t tell you why your company exists, you’ve already lost. Anchor every deal in mission, vision, and values.

👉 Train for connection.
Teach reps to read the room, grab attention in 15 seconds, and tell stories that stick. That’s emotional enablement.

👉 Build unshakable trust.
Be the vendor who tells the truth even when it’s not convenient. 


That’s how you win loyalty AI can’t automate.
AI will level the field. Culture will tip it back in your favor.

Go check the full framework in the carousel above for more insights! 👉

CEO @ SellMeThisPen.ai - AI Roleplay & Individual Sales Coaching at Scale.

The Culture Driven Sales Framework - SMTP

When everyone’s powered by AI, culture becomes your advantage.

When every competitor has the same data, same tools, and same efficiency…what’s left to set you apart?


On the latest SellMeThisPen Podcast, I sat down with Kelly Wright former EVP of Sales at Tableau, ex-President & COO at Gong, and now founder of Culture Driven Sales. We talked about how AI is making sameness the norm and why your culture will be what breaks you out of it.


“If your people can inspire, motivate, and communicate in a way that makes others believe they’re part of something special, that’s the real differentiator.”


At Tableau, in addition to traditional sales training, they trained the entire sales org in storytelling. Every rep learned how to connect emotionally first, then sell. The results? 

Customers started saying “Your team feels different.” Prospects trusted them before the demo even started.That’s the power of culture, it shapes how your people show up long before the pitch begins.


👉 Start with your “why.” Before the product, sell your belief. People buy from conviction, not comparison.

👉 Enable connection, not just conversion. Emotional intelligence beats perfect talk tracks every time.

👉 Protect your mission internally. When your team believes, your buyers feel it.


In the full episode we cover:

– The shift from sales driven to culture driven organizations
– Storytelling as a competitive advantage
– How companies lose (and revive) their “why”
– Why AI will make culture your ultimate differentiator


What’s your take -> can belief still win in a data driven world?

P.S. Link to the full episode in the comments! 👇

Natural talent is the worst predictor of sales success.


So why do so many teams still hire for “the vibe” instead of the mindset?


On the latest SellMeThisPen AI Podcast, I sat down with Thomas Waites of TW Sales, operator behind 3 successful acquisitions, and someone who’s built multiple high-performance sales orgs from scratch to unpack this exact mistake.


"I watched 'natural' salespeople plateau while awkward, determined ones surpassed them."


Thomas learned this early. He’d onboard 20–40 reps at a time and assume the charismatic ones would win.

They didn’t.

The “naturals” coasted…then stalled!


The “awkward but hungry” reps kept grinding then sprinted past everyone.
That observation shifted everything for him.
Because the real problem wasn’t skills.
It was the system those skills lived inside.


He told a story about inheriting a team where people complained about 9 a.m. meetings because it interfered with their morning golf routine.

That wasn’t a skills issue.

That was a mindset and behavior issue and no amount of training fixes that.

So he rebuilt the culture from the ground up.

Reps stopped blaming leads.
Ownership went up.
Performance followed.


Here’s the framework Thomas shared for building a winning environment instead of a “talent-dependent” one:

1️⃣ Hire and bet on mindset first
If someone owns their performance, you can develop everything else. If they blame the world, nothing you do will matter.

2️⃣ Create systems that lift the entire team
Peer-to-peer pairing, shared wins, and simple metrics make improvement unavoidable not optional.

3️⃣ Lead with belief, not fear
High performers don’t need pressure; they need support. If you treat them like losers, they’ll play like it. If you treat them like champions, they rise.

4️⃣ Reward behavior as much as outcomes
Crushing quota isn’t enough. If someone poisons culture, they’re a short-term win and a long-term loss.

If you want a team that keeps improving, you don’t build around the naturals.
You build around the mindsets that scale.


Swipe through the carousel above for the full breakdown! 👉

 7 Pillars for Building Winning Mindset - SMTP

AI didn’t make L&D easier, it exposed who’s been coasting!


So the real question is…are you actually using it to level up, or just hoping it replaces the work you don’t want to do?


The other day on the SellMeThisPen AI Podcast, I sat down with Jen Rutsky an L&D leader with a legal background who’s been hands-on with AI long before it went mainstream. She’s worked across tech, law, finance and she’s one of those  operators who actually experiments instead of theorizing.


Jen described a shift she’s seeing: most L&D orgs still cling to e-learning modules that nobody remembers 20 minutes later. Meanwhile, learners want interactive, kinesthetic, real-time practice. And AI finally makes that possible.


She told a story about managers preparing for tough conversations. Traditionally, they’d wait for Jen to role-play with them assuming her calendar wasn’t booked for the next two weeks. Now? They can fire up a tool, simulate the scenario, and get coaching instantly. No embarrassment. No bottleneck. No excuses.

That’s the shift:

We’re not building courses anymore. We’re building systems that adapt.

Here’s the core idea: L&D relevance now comes from teaching people how to use AI not from producing content.

1️⃣ AI is the new practice field.
Your learners shouldn’t wait for workshops. They should rehearse critical conversations, pitches, and decisions inside AI-driven role-plays, the reps are unlimited, judgment-free, and instant.

2️⃣ Your value is orchestration, not instruction.
Jen’s building workflows, coaching layers, feedback loops. AI handles the repetition; humans handle the nuance. L&D pros who cling to “content creation” lose. Those who build systems win.

3️⃣ Real-time relevance is now the standard.
If a document, process, or naming convention changes, AI can update onboarding flows instantly. No more outdated links, stale PDFs, or credibility-killing errors. L&D finally becomes current instead of catching up.


In the full episode we cover:

– Why e-learning as we know it is fading fast
 – How managers should approach hallucinations with “trust but verify”
 – Building AI champion programs inside companies
 – What modern onboarding looks like when every persona gets personalized learning from day one

L&D pros -> what’s one AI use case you’ve tried that actually moved the needle?

P.S. Link to the full episode in the comments! 👇

Your L&D team isn’t slow. Your workflow is outdated.


The other day on the SellMeThisPen AI Podcast, I sat down with Jen Rutsky, Senior L&D Manager at Yext with 15+ years across banking, tech, fintech, and law. We dug into what’s actually breaking L&D’s speed and what AI is finally fixing.


“It’s helping me amplify my ideas and catch things I might’ve missed.”

Jen shared a moment every L&D leader knows too well: juggling too many trainings, rewriting the same ideas 10 different ways, and manually hunting inconsistencies across documents.

It’s exhausting. And worse, it slows down how fast the business can move.
Then she stopped doing it alone.


AI became her always-on co-author, spotting patterns, surfacing repeated themes, and keeping messaging tight across every training touchpoint.
 The shift wasn’t about shortcuts, it was about finally removing the parts of L&D that shouldn’t be manual anymore.


Here’s the core idea: L&D isn’t broken, old workflows are. AI gives you back the time to think, not just produce.


1️⃣ Offload the grunt work, keep the judgment.
Let AI scan PDFs, books, and decks for themes so you can focus on designing experiences, not cleaning data.

2️⃣ Use AI to maintain consistency across everything.
Jen uploads materials and instantly spots mismatches, outdated details, and messaging drift something humans miss simply because we’re too close to the work.

3️⃣ Turn brainstorming into a real collaboration.
Instead of staring at a blank doc, she uses AI to challenge her thinking, propose angles, and pressure-test concepts. You get better ideas, faster.


The result? Faster content, tighter messaging, and an L&D engine that finally matches the speed of the business.


Swipe through the carousel above for the full breakdown! 👉

6 Practical Ways to Use AI in L&D - SMTP

Most sales leaders don’t coach…they command.


Why are we still defaulting to “just do this” leadership when coaching creates the real top performers?


On the latest SellMeThisPen AI Podcast, I sat down with Thomas Waites, 3X acquisition CRO and the guy who keeps turning messy early-stage teams into record-breaking ones.


"Telling solves the moment. Coaching changes the rep." 


Tom shared something most leaders don’t want to admit: the majority of “coaching” inside sales orgs is actually just instructions with better punctuation. 

And when you lead that way? You create a team that waits for answers instead of creating them.


The shift came when he realized his team wasn’t lacking talent, they were lacking belief, ownership, and a system that helped them think.


Here’s the real difference between telling, training, and coaching. pulled straight from Tom’s winning-culture framework:

1️⃣ Telling -> One-way and urgent.

When a rep asks what to do with a deal, you say: “Send the contract today.”
Fast? Sure. But now you’re the crutch they lean on forever.

2️⃣ Training -> Knowledge without judgment.

You run sessions on your pitch, your product, your frameworks.
Helpful until the deal goes sideways and the script can’t save them.

3️⃣ Coaching -> Two-way, empowering, and culture-shaping.

 Rep: “What should I do with Acme?”
 You ask:
 – “What’s the real blocker here?”
 – “What options do you see?”
 – “Which path gives us the highest leverage?”

Now they think. They decide. They grow.
And suddenly, the whole team levels up, together!


In the full episode we cover:

 – Why mindset beats sales skills (and why “naturals” often plateau)
 – How to build a team culture where “we all win together” actually means something
 – The CEO–sales leader dynamic that predicts success
 – The simple, four-metric system Tom uses to scale without chaos

AND he tells the tattoo bet story, the moment his team realized their limits were self-imposed!! 

Link to the full episode in the comments 👇

ComplyAdvantage

Head of Customer Acquisition, Americas

Building and leading an elite playbook
salesforce across the Americas.

GTM Director, Americas

EliteGTM

Member

Catchpoint

Customer Acquisition Leader
- Adapt GTM
- Refine Messaging
- Establish and own Outbound Business Development
- Lead teams of SDRs, BDRs, and AEs to prospect, nurture, and close new G2000 logos using “the playbook.” (MEDDPICC + CotM)

 Catchpoint is the Internet Resilience Company™.  The top online retailers, Global2000, CDNs, cloud service providers, and xSPs in the world rely on Catchpoint to increase their resilience by catching any issues in the Internet stack before they impact their business. The Catchpoint platform offers synthetics, RUM, performance optimization, high fidelity data and flexible visualizations with advanced analytics. It leverages thousands of global vantage points (including inside wireless networks, BGP, backbone, last mile, endpoint, enterprise, ISPs and more) to provide unparalleled observability into anything that impacts your customers, workforce, networks, website performance, applications and APIs.

Vice President Enterprise Sales

Anchor

Make Date Theft Irrelevant. Anchor It™.

Anchor is a file security platform, built on zero trust principles, that enables the complete ownership and control required to prevent data theft, with the transparency and simplicity users demand.

Simple | Transparent | Affordable
https://anchormydata.com/

Head of Sales and Growth

BMC Software

FY21 Doubled Half Year Plan + Attained Full Year Plan in 6 months + double digit sales growth Year on Year

Management responsibilities for the Digital Service and Operations Management Business Unit's sales business across the US East territory. My team of 8 are intelligent, driven, and accountable professionals focused on driving customers' business outcomes, setting new standards for professionalism in account management.

We work to help drive the transformation of the digital enterprise and bring tangible business outcomes through technological evolution and adoption.

Sales Leader - Digital Service and Operations Management (US East)

VVL Systems & Consulting

Executive Vice President

Delphix

Championed, pioneered, and co-led a core message shift away from a focus on IT Operations, to the new focus on Application Delivery.

Served as the primary product evangelist operating in the live event, video, and blog mediums. (http://www.adam.today &  https://vimeo.com/adambowen)

Served as a cross-functional executive across global field organizations, provided deal support, and technical thought leadership. Aligned with EMEA SVP to collaborate on territory GTM and account strategy resulting in continual record YoY growth.

Co-authored the channel partner program creating and aligning the go-to-market, enablement, and growth strategies.

Co-created an internal cross-functional community of employees known as a "guild." The guild allowed the company to eliminate silos of knowledge; raise the level of competency across the company; and rapidly identify, close, and expand more opportunities with minimal friction.

Established and maintained strategic partnerships with other technology companies to help strengthen market position, more fully tell the company story, and maximize customer value. 

Participated and contributed to product strategy.

Participated and contributed to product prototyping.

Authored the core product demonstration, incl. the surrounding technology stack, presentation, and delivery mechanisms.

Sr. Director EMEA Operations, Global Practice Lead - DevOps and Cloud

Doing all the normal CTO things: listening, researching, building, and evangelizing.

As a DevOps practice owner, I firmly believe customer obsession first begins at home, and is reflected by how you help your teammates pursue greatness and eliminate the things that stand in their way.

My passion is seeking out complex problems, breaking them into their simplest components, and then helping others to overcome them piece-by-piece. 

I am at my best when I am helping others and speaking to a large audience.

Strategic Advisor, Office of the CTO

Chartered, built, and managed the Cloud and Automation Practice for BMC Federal Software. By the time I left, we had grown to a team of 10 and were contributing $MM in revenue per year. The practice was very profitable and was considered one of the premier organizations in the company. I was blessed to receive multiple awards on behalf of our team.

Practice Manager

BladeLogic

Sr. Consultant

Hunches are history. Wave farewell to the perpetual war rooms caused by APM. | Proud Catchpointer | Former BladeLogic/BMC/Delphix

I've been serving as an executive leader in the software industry for over two decades. I am passionate about servant leadership and centering all transformation activities (business and technical) around the people who are impacted. Technology is merely a way to enrich our employees' and customers' lives, and we must always seek out the path that serves our people best.

I have extensive experience in public speaking, vlogging, blogging, and general evangelism; building and leading global services and sales organizations; developing go-to-market initiatives, creating and managing channel programs, field operations strategy and execution, and product marketing.

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