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Sales Executive

We are seeking a passionate and experienced technology Sales Executive looking to drive results by supporting, coordinating and managing a growing sales discipline within our organization.
Remote - Anywhere in Canada
4+ Years Experience

Job Description

We are seeking a passionate and experienced technology Sales Executive looking to drive results by supporting, coordinating, and managing a growing sales discipline within our organization.

Successful candidates must understand the consulting and solution selling space, understand how to manage the sales process from lead qualification to opportunity completion, could form and grow relationships and personal networks, and be passionate about growing the 2toLead brand. The role will require independence, the ability to self-manage, continuous learning, and the ability to work well remotely.

What is different about this opportunity?

As a generous consulting company, 2toLead prides itself on taking a generous, conscientious approach to our services which focuses on providing high-quality interactions, providing meaningful value to those we engage with, and ensuring we take an advisor-first approach.

Your responsibilities will be two-fold: (1) deliver rapid business value for clients by leading a portfolio of projects and project teams; (2) act as a genuinely collaborative partner for clients (identifying, building, and scoping opportunities and improving account leadership as a result).

We have no shortage of demand. We are growing fast, and there are a lot of opportunities for leadership, delivery excellence, and more. Even better, if you are a talented Microsoft technology expert, strategist, or practice lead, all your other skills can be leveraged as we tailor the role to fit you.

We all work remotely and have been working remotely since the company started many years ago. We understand what it takes to be successful and scale and invest in company retreats, offsites, and healthy remote work culture. We are also a high-performance team with leaders passionate about growing your skills and career while offering generous salaries, bonuses, and benefits. You could get equity and an ownership position here at 2toLead and benefit directly from the growth you help drive.


This role will be a mix of execution and leadership responsibilities:

  • Further building out the tools, processes and systems for a scaling sales function at 2toLead.
  • Evaluating current sales practices and procedures to determine whether they are effective in generating sales.
  • Recommending and implementing improvements to current sales practices and procedures as needed.
  • Collaborate effectively with executives and practice leaders internally to help further sales strategy and lead our business development pursuits.
  • Collaborate with the Delivery and Sales teams to get visibility into future opportunities and what we are pursuing and ensure it is reflected in the sales pipeline.
  • Support deeper penetration at existing 2toLead clients through project and support services opportunities.
  • Thoughtfully qualify client opportunities related to cloud projects, either originated from partners, 2toLead lead generation, or other 2toLead connections.
  • Lead, support and close 2toLead client opportunities and manage the entire sales lifecycle.
  • Be responsible for millions in revenue for our consulting and development services.
  • Partner with key stakeholders in 2toLead's partner ecosystem to ensure coordinated and synchronized messaging across all touchpoints.
  • Deliver, develop and support presentations to partners, prospective clients, and existing clients and help to communicate the firm's core values and past outcomes to generate excitement about our services.
  • Develop and share sales collateral. Such as leading and supporting the writing and review of RFP responses, statements of work, and sales presentations summarizing our proposal(s).
  • Preparing, prioritizing and adjusting sales data to inform more accurate sales forecasts to assist the company in making sound business decisions.

Ways to drive more impact

  • Create a personal brand and network within our industry's footprint to help advertise 2toLead's capabilities, model, and competitive advantage in the marketplace.
  • Hiring, training, and developing members of the sales team.
  • Developing compelling material with our delivery and marketing teams on effectively answering common customer and prospect questions.
  • Proven record in building, leading and scaling a successful Sales Team.
  • Technology change management experience and an understanding of common challenges with Microsoft 365 rollouts.
  • Perform competitive intelligence on the client's landscape to uncover trends, best practices, threats and provide recommendations.
  • Create or inform Go-To-Market plans for new products or services by defining customers, segments, and channel strategy.


Having these skills sets you up for success early on:

  • Proficiency in sales management and Customer Relationship Management (CRM) software such as Dynamics CRM.
  • 4+ years of previous sales and account management experience, ideally within a services/consulting environment.
  • Prior experience qualifying and selling technology solutions and services, ideally within the cloud, productivity, or the digital workplace.
  • Proven experience generating millions through the sales of services and or software solutions.
  • Passionate about sales and technology; prior exposure to Microsoft, or cloud applications a plus.
  • Excellent collaboration, relationship and team-building skills.
  • Proven track record of partnering with clients to understand their organizational needs and recommend solutions that add value to their business.
  • Strong verbal and written communication skills; strong customer service and interpersonal skills.
  • Gravitas - candidate should be able to engage naturally with executives and be a person that others seek out.
  • Organized and possess strong prioritization and negotiation skills.
  • Strong process orientation coupled with an ability to work with virtual teams.
  • Experienced in building relationships with CXOs and business decision-makers.
  • Experienced and adept at aligning teams to work toward a common goal; consistently demonstrates strong leadership skills.
  • Demonstrated experience leading sales pursuits from identification to close.
  • Be an entrepreneur at heart. Creative and innovative with the ability to take an idea and run with it.

Thanks for taking the time to apply!

Interview Process

We would love the opportunity to meet everyone who applies, but unfortunately, that is not possible. We will only reach out to those who are short-listed. As part of our interview process, you will have an opportunity to connect with our leadership team to answer why 2toLead is the best place to work, meet one of our Practice Lead’s for a thorough interview and connect with your peers with whom you would work with daily.


Whether you are based out of Vancouver, Calgary, Toronto, Montreal or somewhere else in Canada, you can apply. We are a remote-based startup that strives for work/life balance and supports flexibility so that you can work from anywhere.

You will love the way we work. Together.
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