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

Lotus Financial Services

Creating and leading the business development strategy, helping identify growth opportunities, and improving sales efficiency for sustainable adoption. 
Executing, coaching, and iterating the sales development process, alongside the methodology, through campaigns, hiring profiles, training, and enablement, to hire the first SDR/Jr AE.

Business Development Manager

lululemon

Driving and executing the store KPIs for growth, month after month through coaching, and development of the stores' Educators on discovery, product knowledge increasing UPT and conversion.

Key Leader

ClassPass

Full sales cycle, experienced, hands-on, goal-oriented, process-driven, and strategic thought partner, driving and leading the sales process from outbound activity, qualification, intro, and demo through closing. Brought on new partnerships including multimillion-dollar wellness businesses and fitness studios, in a fast-paced, hyper-growth startup environment, cultivating relationships with key decision-makers in the industry using strategic selling skills.

✭Top LTC ratio of 59%, 
✭July MVP
✭ Created and executed the GTM strategy for the Okanagan (Greater Vancouver) market closing the first deals in the new market
✭Maintained average quota attainment of over 115% (achieved 138% of quota in the first full quarter)
✭Secured a ~30% price reduction for clients on new business by showing greater ROI/revenue over the long term
✭Spearheaded coaching of new AE’s from lead generation to close, which increased closing by 78% over the previous month’s average.

Senior Account Executive

Equinox

Passion for driving results through leadership, coaching, and fitness for club members
✭Fostered relationships to build up class counts, 
✭Increased the number of classes taught by 50% by delivering on coaching and a memorable experience
✭Formalized continued education on innovative content and tapped into mentors to continue to expand my brand

Group Fitness Instructor

TIAA-CREF

Full sales cycle hunting, creating and leading the B2B GTM strategy, captaining positioning College Savings as an employer financial wellness benefit as part of a start-up within the larger company, developing and executing the Benefit Broker strategy and the B2C HNW opportunity. Proactively researched and managed high-value deals quickly establishing trust with key stakeholders and advisors. Quickly established trust with key stakeholders, with the ability to leverage my network and industry contacts to build a sales pipeline (3x quota) through a strategic blend of targeted account acquisitions, tapping new markets and referrals. Identified advantages and key differentiators as compared to competitors within our various markets. Led the sales development process, methodology, campaigns, training, and enablement of new AE’s helping the team negotiate and close deals.

✭Initiated and managed relationships with key enterprise customers; writing the business plan resulting in 120% ($1~MM) increase in division revenue YoY, landing 15 companies topping the tech food chain: Amazon Films, PlayStation, Splunk, NVIDIA, SAG-AFTRA, Google 
✭Developed and led the GTM strategy for ~$100 million Benefit Broker/SHRM market segment
✭Created and executed the internal strategy utilizing internal 401k Advisors, enhancing our cross-selling initiative, and closing on major clients: NYU, Brown, Boston Med, Dana Farber Cancer Institute
✭Elevated the team’s performance through coaching and development, winning new strategic clients and expanding on our revenue targets. 
✭Top closing rate of 32% 
✭Average deal size: $250m +

✭ Vanguard Award: Top Quota driver B2C and B2B
✭2017  Lynch Pin Award: Top Enterprise B2B Business Penetration
✭2016  Retail Products Group All Team Award

Senior Account Executive & Relationship Manager

Various Companies

Sales Consultant

Natixis Global Associates

✭Surpassed team goal of ~$900M in gross Investment Only sales by ~35%.
✭President’s Club award

Regional Director

Wells Fargo Advantage Funds

✭Beat $100M and $250M sales goals in the first two years in a previously unpenetrated channel 
✭Exceeded $500M sales goal by spearheading a multi-faceted sales training program;
✭Grew penetration by 30% by strengthening HD Vest partnership
✭Silver Spoke and Gold Spoke 
Regional Account Manager (Jan 2004 – Jan 2007), 
Associate Regional Director (Feb 2003 – Jan 2004).

Regional Account Manager

UNICORN triple-threat: DEVELOP through creating and iterating the sales development process, and methodology. GROW with a hunter mentality initiative. QUOTA CRUSHER with a consistent and Repeatable Process. Specializing across the spectrum with deals of all sizes from SMB to Enterprise and multiple verticals across FS, Wellness, Tech, etc

*DEVELOP: Boost the team’s performance by mentoring alongside coaching-training of an ideal buyer persona, negotiating and closing deals, as well as solution selling among the team, driving average deal sizes up from $1m to double-digits and developing strategies to help the team meet their targets.

*GROW: HUNTER who THRIVES on challenges and winning high-visibility deals: I’m client-obsessed with a drive for results and a track record for exceeding quotas. I will take those calculated risks and execute them, successfully overcoming sticky objections and a creative problem solver for my existing clients, finding new growth opportunities through FARMING.

*QUOTA CRUSHER: demonstrating influence with decision-makers across all levels with a proven track record of delivering sales pipeline at large enterprise accounts with an average deal size of $250m +, increasing revenue YoY by $1mm +, delivering competitive solution selling, and closing new customers through referrals, creating that repeatable process.

taplio

The Battle

Waylon McGill

Jen Benson

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