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Sales leadership

Regional Sales Director

Keyloop logoKeyloopRemote from CanadaListed 4w ago

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The posting

Keyloop bridges the gap between dealers, manufacturers, technology suppliers and car buyers.

We empower car dealers and manufacturers to fully embrace digital transformation. How? By creating innovative technology that makes selling cars better for our customers, and buying and owning cars better for theirs.

We use cutting-edge technology to link our clients’ systems, departments and sites. We provide an open technology platform that’s shaping the industry for the future. We use data to help clients become more efficient, increase profitability and give more customers an amazing experience. Want to be part of it?

About the role

Reporting to the National Sales Director, this is a managerial role as part of the Regional Sales Team. The Regional Sales Director will be responsible for generating dealer sales growth across their team of Regional Sales Managers. The Regional Sales Director will work closely with the VP, Sales – Canada, the National Sales Director and other team members to create marketing and sales strategies for use by their Regional Sales Team to promote Keyloop Canada products and services.

The successful candidate will be able to demonstrate a strong track record of sales team management, ideally within the automotive market. Extensive collaboration will be required across multi-function teams. A successful candidate will understand the automotive industry and the key challenges, have excellent interpersonal and relationship building skills, demonstrate resilience and be committed to a performance culture.

The candidate will ideally also have a good experience (user or provider) of the Keyloop solutions. A pro-active approach to continuous improvement and a ‘can do’ attitude is essential along with a strong sales management background.

Key headlines

  • Quota carrying sales director for the territories they are accountable for.
  • Overall responsibility of the on-target growth of Keyloop solutions within the assigned territories.
  • Work in collaboration with the Product Sales Managers, in-market Layered Apps and Sales Enablement teams to achieve desired results.
  • Close collaboration with the Keyloop Product Management team to ensure great product/market fit.
  • Work from home office with anticipated quarterly trips to either Winnipeg or Montreal head office.
  • Weekly team meeting and monthly face to face team meetings.

Duties and Responsibilities

  • Deliver on sales objectives as per the company strategic and sales operating plans for the Regional Sales Team within assigned territories.
  • To meet those sales targets through management of the Regional Sales team members and partnering with the Layered Apps team to identify opportunities and conducting joint sales presentations.
  • Prepare and deliver sales presentations and product information sessions to C-level individuals (and other management positions) at dealers and dealer groups.
  • Contribute to marketing and sales strategies for the various products and services that Keyloop Canada offers to dealers
  • Produce Monthly and Quarterly Sales Plans for the markets.
  • Weekly Opportunity reviews in partnership with the Product Sales Managers and National Sales Director.
  • Ensure Regional Sales Team is updating sales activities and pipeline on a daily and weekly basis.
  • Responsible for production of accurate monthly, quarterly and annual forecasts for the assigned territories.
  • Implement and utilize fully the Keyloop Sales Model & Core Processes.
  • To work closely with the Layered App Teams to ensure a joined-up approach and presentation to the customer of ‘One Keyloop’.
  • Work closely with the Keyloop Canada delivery team to help coordinate product delivery and to help streamline processes to ensure delivery is as efficient as possible.
  • Work closely with the delivery team to ensure client expectations are managed in accordance with Keyloop Canada productivity.
  • Provide unparalleled customer service to all Keyloop Canada clients to ensure best-in-class service and support at all times.
  • Very close collaborate with the Sales Enablement team to help produce sales support material for the regional portfolio team members.
  • Overseeing the knowledge transfer / Sales Enablement of all Keyloop Portfolio products within the assigned territories.
  • To feedback market intelligence to increase the internal market knowledge of competitor products.

Knowledge and Experience

  • Minimum 10 years’ sales experience.
  • Minimum of 5 year’ of sales management experience.
  • Significant experience within the automotive sector.
  • Significant experience selling SaaS, cloud-based solutions.
  • Experience managing sales teams that consistently deliver on targets.
  • Excellent communication skills.
  • A proven track record of team sales quota attainment (achieving and overachieving).
  • Customer focused - maturity and diplomacy to manage engagement at varied levels within the target client organisations.
  • Able to implement a professional structured sales approach incorporating Prospecting, Contact Management, Qualification, Presentation, Objection Handling and Closing Techniques.
  • Self-driven, ambitious, resilient, highly motivated, competitive, resourceful, excellent communication skills, especially around listening, questioning – politely assertive.
  • Highly organized within a process orientated environment. Computer literate and familiarity with SF.com an advantage

Skills and Abilities

  • Customer focus skills, also known as customer-centric skills, refer to the abilities and qualities that enable individuals and organizations to prioritize and meet the needs, expectations, and satisfaction of their customers or clients. These skills are essential in business and service-oriented industries where customer satisfaction is a key factor in success.
  • Communication skills refer to a set of abilities and competencies that enable individuals to effectively convey and receive information, ideas, thoughts, and feelings with others. These skills are crucial in personal, social, and professional contexts, as they determine the quality of interactions and the success of conveying messages.

Why join us?

We’re on a journey to become market leaders in our space – and with that comes some incredible opportunities. Collaborate and learn from industry experts from all over the globe. Work with game-changing products and services. Get the training and support you need to try new things, adapt to quick changes and explore different paths. Join Keyloop and progress your career, your way.

An inclusive environment to thrive

We’re committed to fostering an inclusive work environment. One that respects all dimensions of diversity. We promote an inclusive culture within our business, and we celebrate different employees and lifestyles – not just on key days, but every day.

Be rewarded for your efforts

We believe people should be paid based on their performance so our pay and benefits reflect this and are designed to attract the very best talent. We encourage everyone in our organisation to explore opportunities which enable them to grow their career through investment in their development but equally by working in a culture which fosters support and unbridled collaboration.

Keyloop doesn’t require academic qualifications for this position. We select based on experience and potential, not credentials.

We are also an equal opportunity employer committed to building a diverse and inclusive workforce. We value diversity and encourage candidates of all backgrounds to apply .

"At Keyloop, AI is a daily ally: We encourage and train every employee to use our AI tools to boost their creativity and productivity."

Where you can sell from

Fully remote, for people based in Canada.

Taken from Keyloop's own posting, last seen live on 14 Nov 2026.

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The application

Your details and CV, then 14 questions (6 written).

Have readyCVLinkedIn (optional)X profile (optional)GitHub (optional)Portfolio (optional)Website (optional)
  1. 1.
    Which location are you applying for?Pick one · optional
  2. 2.
    What is your age range?Pick one · optional
  3. 3.
    Do you consider yourself to have a disability or be differently abled?Pick one · optional
  4. 4.
    Were you previously employed by Armed Forces?Pick one · optional
  5. 5.
    Are you currently authorised to work in the country of the job without any restrictions?Yes or no · optional
  6. 6.
    Will you now or in future require visa sponsorship to work in country of the jobYes or no · optional
  7. 7.
    Please confirm type of right to work documentShort answer
  8. 8.
    What is your experience with AI Tools like Claude?Written answer · optional
  9. 9.
    Where are you currently based?Written answer
  10. 10.
    Have you previously worked in the automotive or SAAS or software sector? If yes, could you briefly describe your experience?Written answer
  11. 11.
    Please include team size, quota responsibility, and any notable growth or performance outcomes.Written answer
  12. 12.
    We're interested in your understanding of dealer groups, automotive technology, and customer challenges.Written answer
  13. 13.
    What is your current notice period?Pick any: Available immediately · 2 weeks · 1 month · 2-3 months · More than 3 months
  14. 14.
    What are your salary expectations for this role?Written answer

From Keyloop's apply page, checked 12 Nov 2026.

About Keyloop

Dealer management, sales, service and customer retention software sold to car dealers, dealer groups, carmakers and auto financiers outside the US.

Pay schedule: Salaried employment with performance-linked pay the postings do not spell out; Canadian and UK field seats travel to dealers, and the financier account director's book is global with regular international travel.

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