Salesforce

Regional Vice President, Mid-Market Canada at Salesforce

Pavilion

Executive Member

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Enterprise Account Executive (via WJM Ventures)

Vendr

*Role was eliminated when the enterprise segment was deprecated due to product market fit issues.

Led the enterprise sales organization reporting directly to the CEO. Team consisted of 3 sales leaders, 14 enterprise AEs and one strategic enterprise AE.

• Hired 4 AEs, 1 Manager and coached one IC to first manager position

• Helped lead transition from inbound focused team to outbound focused, including increasing AE outbound opportunity creation by over 500% QoQ (Q4-Q1)

• Launched MEDDPICC deal qualification framework across the global sales organization. Responsible for building and delivering training content, collaborating with Sales Operations to build MEDDPICC into SFDC, as well as incorporating MEDDPICC into our sales process and forecasting methodology.

• Architected and implemented a new company-wide sales process including updated deal stages, forecast categories, stage exit criteria etc. Led org wide training on the new process and collaborated on a sales process 1-pager collateral

• Maintained an average of over 7 client facing meetings per week as a 2nd line leader

Director of Sales - Enterprise

Hired to lead a team of 7 enterprise account executives focused exclusively on new business acquisition, selling into Finance, IT and Procurement personas.

• Updated ideal candidate profile and revamped hiring process, implementing Who: The A Method for Hiring topgrading methodology

• Hired 3 Account Executives

• Primary activities were co-selling and coaching, averaging over 12 client-facing meetings per week

• Collaborated with a small tiger team to develop competitive messaging and competitive selling framework

Sr. Manager Enterprise Sales

Plato 

*Sales and marketing functions were eliminated when the company decided to pivot to a new product.

Executive team member and sales leader who guided business strategy and led development of a scalable sales engine and partnership program. Developed forecasts using waterfall methodology and built corresponding sales capacity models. Established tech stack, including SFDC, Gong, Outreach, & ZoomInfo.

• Scaled team from 3 to 12 (4 AEs, Director of Partnerships, Director of BDRs, and 6 BDRs) and hired a front-line leader in <6 months. Created sales compensation plans for AEs, BDRs, and Partnerships program.

• Created and launched outbound sales motion with 6 BDRs generating ~$1M in pipeline within 5 months, closing first deal in <1 month; oversaw creation of 12 & 15 step buyer-persona-driven cadences. 

• Closed multiple 5-figure deals in Q1 achieving 96% to quota, and increased average cost per seat by 20%. 

• Coached team, implemented structured 1:1 format with weekly pulse checks, leveraged Sales Impact Academy, and relied on Gong for call training.

• Developed sales playbook, defined buyer personas, established competitive messaging, and launched an ABM approach for selling to VPs of Eng and CTOs at Mid-Market/Enterprise SaaS companies.

Head Of Sales

Indeed.com

Led 6 teams and 50 employees, overseeing hiring, training, professional development, and performance management during cultural/organizational restructure. Ensured delivery of sales goals, managed revenue forecast, and monitored team metrics. 

• Delivered $14M in quarterly revenue (112% to quota in 2021) by developing a motivated and winning culture, increasing employee training, and building stronger relationships with clients. 

• Boosted sales performance from 99% in 2019 to 117% in 2020 by increasing rep productivity over 40%, implementing repeatable selling motions, and co-leading weekly trainings with top account executives.

• Awarded 2020 Top Gun Award and recognized as top Sr. Director in Canada for achieving 117% to quota. 

• Led Canadian market in new product sales (1st of 14 peer organizations in NA), in addition to leading Indeed Canada’s Acquisitions team responsible for new logos. 

• Fostered a culture of growth and professional development, empowering employees to advance in their sales careers and become industry leaders, resulting in numerous promotions.

Senior Director of Sales

Built, coached, and developed a team of high-performing AEs. Drove prospecting, discovery, and positioning of Indeed’s products. Delivered unprecedented levels of new business and revenue growth.

• Finished 1st out of 5 Canadian Mid-Market teams in 2019 with average quota attainment of 97.6% ($14.4M); critical metric in promotion to Senior Director of Sales. 

• Recorded average of $3.6M of quarterly revenue by coaching reps using Keith Rosen's methodology, shifting focus from targeting HR to Operations, and building a repeatable playbook.

Director of Sales

Developed and executed strategic plans for territory and created forecasts to exceed business and revenue objectives. Ran full sales cycles from prospecting to close, and retained accounts to manage and upsell.

• Achieved 188% of new business target and 112% of quota over 7 quarters by networking through accounts and multithreading, identifying unrealized opportunities, and refining sales process.

• Boosted quarterly revenue from $123,653 to $669,260 in 6 quarters and slashed zero billers from 32 to one in 21 months in a locked book of 50 enterprise accounts.

National Account Executive

Clio - Legal Practice Management Software

Hired to drive revenue, accelerate growth, and establish sales development function. Built out the SDR team and function in collaboration with Sales Ops, Marketing, and the SVP of Global Sales. 

• Integral in boosting sales from $10M ARR to $30M ARR over the course of two tenures with Clio as both an IC and sales leader; teams touched 95% of all revenue. 

• Established KPIs, compensation plan, division of labour between SDRs and AEs, and handoff procedure for Sales Qualified Leads; created a book club focused on sales skills and the mental aspects of performance.

• Increased AE close rates by over 15% in first 6 months through better qualification and discovery.

Additional Accomplishments: 

2015 Q3 - 111% of MRR Quota
2015 Q4 - 127% of MRR Quota
2016 Q1 - 142% of MRR Quota

Manager - Sales Development

LinkedIn

Account Executive

Led full cycle sales for Practice Management SaaS product, selling to law firms via managing partners, IT departments and office managers. Onboarded new reps and coached them on closing large deals as third sales hire in Toronto. 

• Closed +40 deals per month to hit monthly sales targets of $5K MRR with an average deal size of $150MRR; recognized consistently as the top-performing rep company-wide. 

• Implemented new talk tracks, created upfront contracts, and leveraged structure & consistency to tighten deal cycles. 

Awards
*2014 Q2 Top Rep
*2014 Q3 Top Rep

Lyreco

Sold office products. Represented Field Sales on a committee with marketing to develop new, more relevant collateral. 

• Received 3 promotions: Account Manager to Account Executive, AE to Sr. AE and Sr. AE to Territory Sales Manager, selling into accounts spending in excess of $50K/year. 

• Top performer out of 120 reps, consistently overachieving targets (130% average) while hitting every President's Club.

Territory Sales Manager

Senior Sales Executive

Experienced sales professional with 15 years experience in selling, building teams and establishing winning cultures. Compassionate leader with a strong focus on recruiting, coaching, co-selling and data driven decision making. Passionate about people, sales and personal development.

Waylon McGill

Product Marketing Alliance

Sales Enablement Society

ClosedWon

Product Marketing Strategy Advisor for B2B SaaS Startups

Fractional Product Marketing Leader/Advisor

Law Insider

When I joined Law Insider in Q4 2023, the company faced several critical challenges. Environmental threats driven by LLMs and AI. The product was largely designed for single-player users, while the existing multiplayer support was hidden behind a sales-gated model that limited adoption. Payment options were restricted to a single plan, leading to widespread password sharing and missed opportunities for revenue growth. Additionally, the leaky churn bucket meant many customers left before realizing the platform’s full value.

To address these issues, I led and collaborated closely with customers, engineers, UX designers, and cross-functional teams to build a platform that could better meet the needs of both individuals and teams, while reducing churn and increasing revenue.

I led key initiatives at Law Insider, including launching a new product (Law Insider Pro) with AI-powered features, redesigning multiplayer functionality for self-serve access, ran quarterly pricing optimization tests, and adding in-app training and weekly training webinars to improve onboarding. We reworked the signup flow to prioritize annual over monthly plans, and launched countless features.

Through these efforts, we transformed Law Insider into a scalable, user-centric platform:
	1.	ARR Growth: (+6.8%).
	2.	Annual Subscriptions: ARR from annual accounts increased from 38.66% → 50.27% (+30.0%).
	3.	ARPA: Improved (+32.6%).
	4.	CLV: Overall CLV grew (+43.1%).
	5.	Churn Reduction: Smoothed churn rate dropped from 6.32% → 4.59% (-27.4%).
	6.	Customer Duration: Extended from 15.82 months → 21.79 months (+37.7%).

These improvements represent more than just numbers—they reflect a business fundamentally transformed:
	•	Customers are more committed with a stronger preference for annual plans.
	•	Accounts are more valuable, contributing higher ARPA and CLV.
	•	The business is more predictable and stable, with reduced churn and longer customer relationships.

Vice President, Product Marketing

Crux

I was recruited to come into Crux to transform a 5 year old data integration service business for the financial services industry into a proper software as a service (SaaS) business for data integration, transformation, and observability. 

Outcome: We scoped, built, priced, packaged, and eventually launched a brand new SaaS in 2023.

Key Accomplishments:

- Developed a combination of usage and seat based pricing and packaging for the new oﬀering. The
approach immediately increased opportunity close rates by 2x within 30 days of rollout.
- Led a team that built customer personas, managed product launches, and successfully repositioned the company into a new category.

Director, Product Marketing

Filled the leadership role for the marketing organization during a CMO search, while continuing to service in Product Marketing Leadership

Key Accomplishments:
- Grew a team of 7 across PMM, Field, Demand Gen, Content and Sales Enablement
-  Promoted within 6 months due to strong performance and organizational impact.
-  Developed and led the Launch of Company Leadership Principles with HR and Executive Team.

Interim Head of Marketing

- Transformed a 5 year old services business into a consumer facing SaaS business.
- Launched new positioning, messaging, and sales material that drove 2x Meeting Velocity.
- Established Product-led Growth function that would lead to achieving 200% of Goal for activated customers.

Sr. Product Marketing Manager

Rasa

Rasa is the leading conversational AI platform, enabling enterprises to build a next-level customer experience.

Outcome: Reduction in force due to global pandemic in Spring 2021.

Key Accomplishments:
- Revamped messaging and positioning leading to 150% increase in conversion from top-funnel signup to close for the enterprise version of the open-source chatbot product.
- Helped the Analyst Relations team achieve first placement on the Gartner Magic Quadrant Enterprise
Conversational AI Platforms.
- Developed an aligned vision for the enterprise product across 5 product teams, revenue, marketing and
operations departments.

Recess.io

Recess was an internal communications and performance management platform for people ops, and company leadership to better communicate and manage their teams. I came into Recess to help build out a product-led-growth marketing function, and to work with customers to understand if we can achieve product-market fit.

Outcome:  Successful exit via Acquisition (Trainual).

Key Accomplishments:
- Established Product-led Growth eﬀorts for email marketing tool for internal comms which led to a 5x
increase in Annual Recurring Revenue.
- Led cross-functional team of engineers in reworking the customer experience which brought the time to value (customer sends their first email) down from 2 days to 2 minutes.
- Led a product relaunch to customers and increased ARR by 4x. within 3 months.
- Created a self-serve customer training and in-app onboarding experience to increase adoption in close
collaboration with customers, executives and technical leads that increased trial conversion rated by 5x.

Head of Product & Product Marketing - (Early Stage Startup)

Senior Product Marketing Manager

A B2B Marketing Agency, ClosedWon's focus is to help marketing teams at high-growth B2B SAAS companies scale through:
- Product Marketing
- Change Management
- Category Design

Managing Director & Founder

HYLA Mobile

Established the B2B sales team.

Outcome: Acquisition

Director of Sales - B2B

eRecyclingCorps was born out of the leadership team at Easysale special project when we
saw that cell phones were piling up in people's drawers. Eventually, we decided to focus solely on mobile devices.

I established all operations for mobile device sales. The initial channels included eBay, Amazon, and an online store direct-to-consumer. It was called wirelessreplacements.com

Through a combination both consumer research strategies & behavior-based
online targeting, I gained new direct & e-commerce customers spanning the globe in the renewable wireless industry.

eRC (now known as HYLA Mobile) believed that by transforming the wireless device ecosystem into an opportunity for renewal, reuse and recycling, they're not only benefiting the environment, but creating an economic opportunity that rewards everyone who participates.

We invented, implemented, and served as the back-end for the process of trading in your phone at the point of sale at carrier stores for carriers in the US like Sprint, Verizon, AT&T, and T-Mobile before expanding internationally.

Director Of Ecommerce

easysale

I was promoted to lead all operations within a main distribution center and a fleet of trucks, and five retail locations in the DFW area.

Outcome: Business narrowed focused on Mobile Devices, becoming HYLA Mobile.

Director Of Operations

Recruited to lead the team at Easysale by former RadioShack executives.

Provided guidance in the creative team room for a dozen copywriters, photographers, and assistants. We wrote copy and provided creatives for hundreds of unique items every day. We once sold a banana for a thousand dollars. The team produced tens of thousands of unique ads in a challenging, fast-paced production-oriented environment.

Head Of Ecommerce

Product Marketing Leader (Player/Coach, Advisor/Consultant)

Build What Sells 🔁 Sell What's Built

👀👇

I’m a curious B2B SaaS leader with deep expertise in product marketing, product management, and go-to-market strategy. My career has been defined by connecting the dots between customer insights, product development, and sales execution—ensuring that we build products people actually want to buy and that sales teams are equipped to sell them effectively.

At my core, I focus on end-to-end customer experience rather than just isolated marketing tactics. I thrive at the intersection of product, sales, and marketing, ensuring alignment that drives revenue growth, customer retention, and long-term value. My background spans customer marketing, marketing operations, and sales enablement, giving me a unique lens on how businesses scale.

Currently at Law Insider, I’ve led major initiatives to increase customer lifetime value and reduce churn by launching a new Pro product tier, optimizing pricing and packaging, and introducing AI-powered features. Previously, at Crux, Drift, Rasa, and DigitalMarketer, I played key roles in product launches, repositioning efforts, PLG strategies, and pricing transformations—helping businesses move from single-player models to scalable, high-retention platforms.

Beyond my work in-house, I’ve owned an agency, been a speaker at Flip My Funnel, PRSA, AMA, and Grow with HubSpot events and have advised companies like HubSpot, Foursquare, and Methodist Health Systems on product marketing and growth strategies. I’ve also led HubSpot User Groups and built customer education programs that drive activation and expansion.

I love making complex products feel intuitive, optimizing pricing and packaging, and driving cross-functional alignment to accelerate growth. If you’re thinking about how to improve retention, scale a SaaS product, or reposition a brand for expansion—let’s connect.

taplio

The Battle

Waylon McGill

Chris Handy 🎉

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