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 👇

Clutch

Director; Sales Enablement

Xero

Success portfolio: Driving a globally adopted onboarding strategy for multiple sales roles in a global fintech organization. Aligning business objectives, to competencies, roles, performance and keeping it fun!

Revenue Enablement Business Partner - Global Onboarding

AMER sales enablement manager, within the global Sales org, supporting a cloud accounting, SaaS, fintech organization with software for SMBs.

• Driving SaaS metric growth with measured and impactful sales training including: toolset, skill set and mindset learning programs that improve the sales workforce learning experience.
• Assess, design, create and deliver virtual, elearning and in-person programs globally including: soft skills sales methodology, onboarding training, product, coaching methodology and change management to leadership and sales across AMER
• Assess current sales and learning tech stack; interview vendors to determine business case for workflow/pipeline efficiencies. Video prospecting, LMS efficiencies, RFP workflow apps, revenue optimizations
• Operate cross functionally with Product, Marketing, Heads of (Sales, Country), VPs, and sell internally strategies as a lever to deliver measured revenue growth strategies

Extras: Head of AMER SEI (Sustainability) organizing volunteer strategies to promote net zero carbon, supporting those experiencing homelessness and other charity events/sponsorship

Sales Enablement Manager

TSCC 2443

Jointly responsible for the decision making of a $3 million dollar budget to improve the life of the residents of Westlake Tower #1 through cost-effective measures.

Successes in 2019:

Reduced maintenance fees 2.1% in Year 1
Changed management to better support residents
Found cost savings through energy reduction efficiencies.

Success in 2020:

Pivoted budget to support Covid measures
Sourced vendors to support corporations' objectives
Navigated a $300,000 fire, with 0% increase to overal operating budget.
Implemented community feedback forums/questionaire. All vendors receiving above 80% grading on quality.

Added Quarterly Town halls and monthly newsletters to better include residents in spending choices and improve transparency.

Success 2021
Implemented SaaS cloud HVAC (Parity) green initiative

Director Board Of Directors

TELUS Business

TELUS Business – Sales Enablement Learning Consultant
Supported the Small Business Solutions (SBS) transformation as an enablement lead. Spearheaded strategic onboarding and training programs to drive rapid growth and sales performance across Canada.

🔧 Program & Instructional Design
Built and launched a national instructional design function using the ADDIE framework across diverse stakeholder groups.

Designed and facilitated a 4-day “Soft Skills for Sales” program, rolled out nationally to boost customer engagement and sales confidence.

🚀 Sales Onboarding & Transformation
Led onboarding strategy during SBS transformation, scaling the sales team from 30 to over 200 reps nationally in under 90 days.

Delivered enablement solutions that directly contributed to reps exceeding performance targets during high-growth periods.

🛠 Enablement Technology & Process Optimization
Improved enablement efficiency by implementing and integrating tools like LevelJump and Salesforce Lightning into the tech stack.

Optimized sales workflows and rep experience through system training and automation enhancements.

💼 Stakeholder Engagement & Leadership
Secured C-level sponsorship and buy-in for enablement strategy through high-impact presentations and business cases.

Acted as a key liaison across shared services, ensuring alignment and communication across teams during periods of rapid change.

🌐 Vendor & Partner Management
Managed vendor relationships and training delivery through TELUS International call centre partnerships.

Oversaw enablement budgets, ensuring cost-effective and timely deployment of national training programs.

⚡ Agile Strategy & Crisis Response
Pivoted national sales training strategy in response to COVID-19 disruptions, maintaining continuity of learning and productivity across distributed teams.

Learning and Development Consultant - Small Business

Rogers Communications

Responsible for the delivery of training initiatives to employees at a national level. These training courses include systems/technology, sales and service level based training and always putting the customer first in everything we do.

Small Business Sales Trainer

Create sales solution training for retail and enterprise sales teams. Using adult education methodologies to deliver compelling and impactful training to develop successful employees and help them build solutions and outcomes for customers. 

Responsible for relationship management, within an assigned territory to ensure retail sales growth through ad hoc training and support.

LMS (Learning Management Systems) experienced.

Develop manager level coaching; material, training, implementing, delivery.



SalesForce and enterprise training specialist.
MS Office/Cloud Solutions training specialist. 
Coaching/Mentoring program implementation specialist 
Run department Social Committee
Onboarding Trainer

Senior Learning Facilitator - Sales

LAUNCH! (By Mosaic Sales Solutions)

-Liaison between the field teams, procurement, training and clients to ensure that campaigns are run successfully with all required tools and within budget

-Manage multiple Shopper Marketing and sponsorship campaigns throughout Ontario and Quebec from the inception of the idea to running the events and reporting on the KPI

-Responsible for ~5 Million in revenue/budget

Client Services Manager

Mosaic Sales Solutions

I spearheaded initiatives that significantly boosted Microsoft’s market share in Ontario through effective team management and strategic training.  

• Oversaw scheduling and delegation, ensuring optimal store performance and team empowerment.  
• Compiled and analyzed key metrics, delivering insightful reports that added value to client relationships.  
• Conducted training sessions that equipped team members with essential skills for success in a competitive market.

Sales Manager

Princess Cruises

2 Winter Contracts*

-Managed a team of entertainment professionals
-Ran activities, to ensure guests had the time of their lives

Assistant Cruise Director

Brand Momentum Inc.

Recruited, hired, trained and managed a team of 30 highly effective in-store technical experts for the Bell Canada FibeTV brand. 

Successful execution of the campaign lead to program extension and future spin off programs for Brand Momentum.

Team Lead/Coordinator - Bell Canada (Contract)

S-4 Sound Sensation

Master of Ceremony 

Set up lights/logistics for hundreds of events including:
Fashion shows
Corporate events
Training Seminars
Weddings
Bar Mitzvahs


Ran inhouse Lighting and Audio Video for ByPeterandpauls.com venues including:
-Paramount
-Belagio
-The Manor

Troubleshooting issues on the fly in a fast paced, event set up environment.

Trained in LightJockey, Serato, Virtual DJ, Traktor, advanced AV troubleshooting.

DJ / MC

Results-driven Sales Enablement Leader with 15+ years specializing in SaaS, Fintech, and digital transformation.

Core Competencies:

🚀 Design and deliver high-impact sales training programs leveraging adult learning principles
🛠️ Build comprehensive sales enablement frameworks that drive revenue growth
📊 Partner with stakeholders to develop and execute strategic learning initiatives
🎯 Transform sales teams through modern sales tools and methodology adoption

Key Achievements:

📈 Architected sales enablement programs driving consistent quota attainment
🔧 Developed comprehensive training frameworks for SaaS and Fintech products
🚀 Led digital transformation of sales training methodologies
📊 Established measurable performance improvement programs

Leadership Philosophy:

Building confident, high-performing sales teams through empathetic coaching and data-driven enablement strategies. Committed to creating sustainable success through kindness and continuous learning.

Industries: SaaS | Fintech | Technology
Expertise: Sales Enablement | Adult Learning | Digital Transformation | Strategic Planning

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