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VP Sales - Convictional

Ready to solve the hardest problems facing the world’s suppliers & buyers? Do you have experience scaling a world-class sales organization, and a desire to build one again? Check out this VP Sales opportunity!

Who Is Convictional & How Are They Changing the World?


Suppliers are the lifeblood of retailers, which should mean it’s easy for them to transact with each other, right? Yes, but with one big, outdated hitch: due to continued reliance on Electronic Data Interchange (EDI), a technology 

that’s been in place since World War II, it can take months for a retailer to onboard a new vendor. Despite knowing what brands their customers want, retailers struggle with stale product assortments, oversold inventory, and stagnating revenue. 


Enter Convictional's Founders, Chris Grouchy and Roger Kirkness, both former Shopify Plus team members who helped launch Shopify’s wholesale channel; they saw an opportunity for global scale disruption.


Convictional is the first supplier enablement platform for retailers and distributors to power drop-ship, marketplace and wholesale business models in one solution. Think Shopify for B2B. With Convictional, businesses can automate and integrate trade, regardless of size or technical expertise. They’re levelling the playing field and connecting suppliers and buyers, regardless of the systems they use. 

Enterprise retailers like Indigo, Staples, Equinox, and Harry Rosen now rely on Convictional’s infrastructure to trade with third-party suppliers. They’ve secured $6.7M in Series A funding led by solo venture capitalist Lachy Groom (who led Convictional’s 2019 seed round out of Y Combinator). With other leading operators, like the former COO of Stripe and the former CEO of Walmart International joining the round, this startup is primed for growth and impact.

How Will I Make An Impact?

Convictional is looking for a highly motivated VP Sales to hire, build, and enable high-functioning teams that grow company ARR at the fastest, sustainable rate possible. As the VP Sales, you will:


  • Deliver on the company’s net new ARR goals quarterly and annually

  • Build a recruiting machine for sales reps, sales managers, and support staff (ops and enablement), and lead the long-term process of creating a talent brand for all levels of sales staff

  • Lead the Enterprise and Midmarket sales team, driving the teams to hit their quarterly and annual goals  

  • Implement a performance culture where sales reps focus on good fit accounts, qualify thoughtfully, and think long-term about customer retention and usage

  • Partner with Product Marketing to create vertical-specific content to serve our market segments, 

  • Partner with Customer Success to create and update sales accepted criteria based on retention

  • Give great feedback to our product management and engineering leaders to move past minimum sellable product for each persona and maximize the long term opportunity

  • Implement and refine the go-to-market strategy of selling to durable Enterprise and Growth buyers based on Board-level forecasts

How Do I Know If This Is For Me?

  • You’re a team builder that has made a significant impact by enabling teams. You’re able to develop and engage ICs and managers (and you enjoy doing it!).

  • You’re data-driven and can define historical productivity metrics, such as recruitment velocity, sales rep ramp time (% change over time), and quarterly team results ($ and % attainment). You can make decisions and improvements based on waterfall metrics.

  • You can hire, develop, engage, and evaluate program managers, support staff, and operations staff to scale sales hiring, enablement, and revops.

  • You’re adaptable and eager to figure things out; you know a rinse and repeat playbook won’t work here!

Our Ideal Candidate Looks Like:

  • You’re an experienced sales leader who has recruited and enabled top enterprise and midmarket sales reps at Series A, B, and/or C stage companies.

  • You’ve turned headcount forecasts into high performing teams.

  • You have experience preparing board-level updates on sales progress.

  • You can set the pace with your energy, kindness, and aspirational work ethic.

Nice to have:

  • You have experience in one of the following domains: B2B trade, EDI, or eCommerce. 

  • You have experience with SMB sales (although our primary focus is on Enterprise & Midmarket)

Convictional is only prepared to hire candidates currently living in Canada and the United States and are unable to consider other international applicants. 


We understand, accept, and value the differences between people of different backgrounds, genders, sexual orientations, ages, beliefs, and abilities.  We aim to create an inclusive environment and encourage diverse individuals to apply.

The Process:

Convictional is hyper-focused on delivering a positive candidate experience. The general hiring process looks like the following:

Step 1: Conversation with your Artemis Recruitment Consultant, Carly

Step 2: Introductory conversation with President & Co-Founder, Chris

Step 3: Conversation with Head of Sales, Vanessa

Step 4: Meet with Leadership Team & Work Evaluation

Step 5: Conversation with CEO & Co-Founder, Roger 

Step 6: References & Offer


And of course, your Artemis Canada Recruitment Consultant, Carly, will work closely with you throughout every step of the process.

We’d love to hear from you - even if you don’t meet 100% of the requirements! Send a note to if you or someone you know is interested!


Does this sound exciting to you?
Get in touch with Carly!

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