Salesforce

Regional Vice President, Mid-Market Canada at Salesforce

Pavilion

Executive Member

SaaStr

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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

ion8

At ion8, we offer a comprehensive services ecosystem that integrates three core areas of business management:

Business Process and Strategy
Our team excels in optimizing CRM and business software ecosystems, navigating federal and provincial grants, implementing cutting-edge software and cloud systems, and developing tailored eLearning solutions. We ensure our clients are at the forefront of operational excellence and strategic innovation.
Software Development and Deployment
Leveraging full-stack engineering capabilities, we create bespoke solutions, integrations, and middleware that drive business efficiency. Our expertise spans web app development, UX/UI design, rigorous security and QA processes, and ongoing maintenance. We also specialize in seamless marketing integrations to amplify our clients' digital presence.
Marketing, Communications, and Design
Our holistic approach encompasses analytics and optimization, intelligent website design, customer engagement strategies, and comprehensive branding services. We deliver data-driven content and SEO campaigns, coupled with targeted advertising and promotion to elevate our clients' market position.

In my role, I'm dedicated to helping organizations leverage ion8's integrated services to achieve unprecedented growth and operational efficiency. Whether you're looking to streamline processes, connect disparate SaaS, or enhance your market presence, I'm here to guide you through ion8's ecosystem of services tailored to your unique needs.
Let's connect and explore how ion8 can propel your business to new heights of success.

Head of Sales

Big Trouble Consulting

Big Trouble Consulting helps visionary founders turn bold ideas into unforgettable brands using AI. We fuse cutting-edge tools like ChatGPT with vibe marketing to build digital identities that feel right and convert fast.

We’re not an agency. We’re your AI-native brand co-pilot.

Founder

OneAdvanced

Prospected, qualified, and closed new business with AMLAW 100 firms, including Seyfarth Shaw and Kirkland & Ellis. Sold proprietary time-recording software (Carpe Diem), NetDocuments, and related professional services. Met or exceeded quotas consistently. Owned end-to-end sales cycle, from outreach to forecasting, using Salesforce for accurate weekly, bi-weekly, monthly, and quarterly projections. Drove sales through automation campaigns, content marketing, and strategic account planning.

Senior Account Executive

ResQ

Owned the entire sales cycle, including lead generation,
qualification, demos, onboarding, and closing for a SaaS enabled marketplace connecting service partners with the hospitality industry. Developed close, trusting, referenceable customer relationships in Chicago.

Mid-Market Account Executive

Clio - Cloud-Based Legal Technology

Responsible for demo to close with annual sales exceeding $1 million ARR. Contributed to securing a $20 million Series C investment led by Bessemer Venture Partners (BVP) and a $330 million Series D investment led by JMI and TCV. Earned two promotions, spoke at law schools and companywide sales
kick off (SKO). Engaged in high-level professional development and networking through participation in symposia ahosted by preeminent legal organizations, including the International Society of Bar Associations, Ontario Bar Association, Ohio State Bar Association, Law Society of Ontario, and the Council of Canadian Innovators.

Government and Corporate Account Executive

Univeris

Prospected and developed relationships with retail wealth management and insurance managing general agency owners in Canada. Implemented new client campaigns in Salesforce leading to new software development and sales opportunities. Conducted market research and analysis to direct new market and branding initiatives.

Sales Director

Amicus Attorney

Surpassed annual, monthly, and quarterly sales objectives. Achieved double-digit growth and repaired channel partner relations. Set revenue records for monthly and quarterly results in company history.

Regional Sales Manager

There is a quiet revolution happening. It's not about the loudest voice or the flashiest product. It's about connection.
At ion8, I'm part of that revolution. We're not just selling software; we're building bridges between cloud, voice and people. 
We connect great law firms and companies with their customers by working with great partners like Clio,   Zoho, RingCentral, Dialpad, PandaDoc, Atlassian and from our own talented team of developers. 
This isn't just about software or SaaS. It's about service.
As part of SaaS partner ecosystems, We've seen businesses transform. Not through grandiose gestures, but through small, meaningful connections. One customer at a time. One solution at a time. One relationship at a time.
Big Trouble Consulting isn't just a name. It's a promise. A promise to tackle the big troubles, to ask the hard questions, to find the hidden opportunities.
I've learned that the medium changes, but the message remains: connect, provide value, make a difference, be better. 
In this noisy world of tech and targets, of quotas and KPIs, remember this: We're not in the business of selling software. We're in the business of solving business problems.

taplio

The Battle

Waylon McGill

Jeremy Secker

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