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Sr. Engagement Managing Consultant

We are seeking a passionate and experienced Microsoft technology Consulting/Engagement Manager looking to drive results by collaborating with senior leadership while advising clients with big-picture and tactical guidance on how technology enables a variety of business outcomes.
Remote - Anywhere in Canada
5+ Years Experience

Job Description

We are seeking a passionate and experienced Microsoft technology Consulting/Engagement Manager looking to drive results by collaborating with senior leadership while advising clients with big-picture and tactical guidance on how technology enables a variety of business outcomes.

Successful candidates must understand the consulting services and solution space and will play a pivotal role in projects crafting strategies, delivering recommendations, and helping our clients with their most pressing issues. You will be responsible for project oversight and delivery, team management, coaching, and developing and maintaining productive relationships with clients.

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:


  • Leading both our Clients’ and our internal project teams from strategy development through to implementation across a portfolio of clients.
  • Managing and developing client relationships across multiple projects and working closely with clients to identify new areas of opportunity for value creation.
  • Build key relationships with business and IT personnel across multiple business lines to deliver project-related requirements.
  • Recommend and implement process improvements affecting multiple teams, technologies, systems, or business areas to increase efficiency.


  • Leveraging your subject matter expertise, experience, and skills in ensuring successful delivery across a portfolio of client projects.
  • Operate as a Digital Employee Experience subject matter expert who can design technical solutions and have the ability to bring 2toLead capabilities to light when linking them to our client’s desired outcomes.
  • Facilitate art-of-the-possible sessions with stakeholders to showcase technology and use cases.
  • Facilitate requirements gathering sessions with stakeholders and business users to capture business rules, workflows, solution goals, and project objectives.
  • Engage with SMEs and third-party service providers to discuss requirements and solutions as necessary.
  • Document business requirements and rules and translate them into functional specifications.
  • Manage an ongoing gap analysis and resolution of gaps with process-driven solutions.
  • Recommend technology solutions and relevant technical processes to solve business challenges (ideally focused on Microsoft technologies).
  • Offer customers design and configuration best practices when aligning and deploying our services.
  • Collaborate with the Sales Team on project estimates and provide a solution-oriented approach.
  • Identify and address risk in our solutions or proposals.

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 delivery team members.
  • Developing compelling material with our delivery, sales, and marketing teams to effectively answer common customer and prospect questions.
  • Prove or establish your record in building, leading, and scaling a successful Sales or Delivery Team.
  • Showcase your impact and experience by helping establish case studies that map to understanding common challenges with Microsoft 365 and Power Platform and how you helped solve them.
  • Perform competitive intelligence on the client’s landscape to uncover trends, best practices, and threats and provide recommendations.


Having these skills sets you up for success early on:

  • Post-secondary education in Computer Science or Information Systems or related qualifying work experience.
  • Proven and demonstrated experience managing and leading a team.
  • Experience working with a professional services firm.
  • Fundamentals in solution cost modelling and business casing.
  • Proficiency in Microsoft Office Suite, including Visio, PowerPoint, and presentation tools.
  • Ability to serve as a trusted advisor in solving challenging technical and business problems.
  • Good relationship-building skills are necessary, including building a rapport and communicating effectively with all levels of 2toLead and the customer.
  • Be capable of building strong, direct relationships with senior technical contacts, comprehending customer architectures and solution offerings for Power Platform and/or Microsoft 365.
  • Be self-motivated, self-sufficient, and able to stay current on emerging industry trends, technologies, and issues.
  • Willingness and ability to learn and work independently with minimal supervision.
  • Years of technical experience with deep knowledge of key trends in Cloud services.
  • Microsoft 365, SharePoint, and/or Power Platform consulting experience is highly recommended.
  • Cloud certification(s) a bonus.
  • Strong analytical and problem-solving skills.
  • Strong attention to detail with a logical and methodical approach.
  • Have excellent presentation skills and experience selling to mid to large enterprise and corporate customers.
  • Effective organization and time management skills with the ability to work under pressure and adhere to project deadlines.
  • Strong interpersonal, written, and verbal communication skills.

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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