Michael Ocean

I’ve been in sales since I was 9 (selling sneakers to my classmates), but my real journey has taken me from founding AE to help scaling sales at companies with hundreds of reps.

And no matter the size of the org, one thing’s always been broken: coaching!

It was always reactive. Training was one-size-fits-all. Role-plays? Rare. Real coaching? Only if your manager wasn’t buried in pipeline reviews. And meaningful, actionable feedback? Practically nonexistent.

That’s why we built SellMeThisPen AI - to help revenue leaders scale personalized coaching and practice without adding more meetings or headcount.

Here’s what it helps you with:

✨ On-demand AI role-plays to sharpen real skills

✨ Instant, AI-powered coaching after real calls or mock sessions

✨ Reinforcement learning that actually sticks

Bottom line: It helps your team ramp faster, close better, and grow revenue - without burning out your managers.

If you’re rethinking how you scale coaching, let’s talk. 🤝

Founder & CEO

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

SellMeThisPen AI is the best role-play and coaching tool on the market. Period.


Now, you might read that and think: “Cocky motha…! 
But it’s not BS, it’s clarity.


Because here’s the truth: “Best” only matters in context.
SellMeThisPen AI is the best product for the right ICP and it might be the wrong fit for others. And that’s okay.

A lot of buyers get pulled in by hype...big promises, bold claims, shiny buzzwords. So buyers should ask smarter questions like:

- What does “best,” “first,” or “most powerful” actually mean in practice?
- Best for who?
- Best for what outcomes?
- And under what conditions?


Where we win is when teams need more than “just a license.”
We don’t stop at workspace setup. We partner with our clients to build real, functional solutions that drive adoption and we share enablement ideas that stick long after onboarding.


And speaking of “best”…
Another perspective: Ranger (our dog) is the best-looking dog in the world.
No debate. No “depends.” He just is! lol

Also: Philly, Baltimore, DC, Pittsburgh, and Cleveland were all great, but Ranger definitely seemed to like Cleveland the most.

Not sure if it was product-market fit, friendlier people, better weather…but the dog has spoken.


Up next → Chicago. Can’t wait 🤘

CEO @ SellMeThisPen.ai - AI Roleplay & Individual Coaching for Client Facing Teams.

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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Michael Ocean

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