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Sales Enablement Manager

Your career is an investment that grows over time!


Wealthsimple is on a mission to help everyone achieve financial freedom by reimagining what it means to manage your money. Using smart technology, we take financial services that are often confusing, opaque and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with over 4 million users who trust us with more than $50 billion in assets.


Our teams ship often and make an impact with groundbreaking ideas. We're looking for talented people who keep it simple and value collaboration and humility as we continue to create inclusive and high-performing teams where people can be inspired to do their best work.


We’re building the world’s most human financial company, using technology to scale the value we provide to our clients, and people to add value where only humans can.  Sales at Wealthsimple is about serving our clients and helping a generation of Canadians reach their financial goals.


The primary focus of Sales Enablement is to empower our sales teams with the knowledge and tools they need to achieve exceptional results. As a Manager in Sales Enablement, you will play a critical role in ensuring our sales teams are equipped with the latest product knowledge, streamlined processes, and cutting-edge technologies. You will not only support our sales teams but also drive the overall success of our sales initiatives by ensuring our content and training programs are both effective and aligned with our business goals.


Today the financial services industry is an oligopoly dominated by five big banks.  They charge high fees, and provide poor service to clients with less than $3M in net worth.  Additionally over $2T in assets are in the Wealth Management sector and a large portion of these assets are investing with high fees and poor returns. We believe that it is time for something different for Canadians.


Wealthsimple is a financial services company on a mission to help everyone achieve financial freedom by providing products and advice that are accessible and affordable. Using smart technology, Wealthsimple takes financial services that are often confusing, opaque and expensive and makes them simple, transparent, and low-cost.


With over 3 million clients and $50B+ in assets, we are the market leader in Canada. Our team is working together to build one of the most innovative fintech companies in the world and we're looking for talented people who want to help us move fast, ship often, and make a huge impact. Join us on our mission to make financial services simple and affordable for everyone!


Read our Culture Manual to learn more about us and how we work.


In this role, you will have the opportunity to:
  • Empower our sales teams to achieve peak performance and exceptional results by improving their knowledge, skills and process adoption 
  • Develop and scale the Enablement program for our Investment Advisor and Financial Planning teams by raising the bar on quality, service and financial knowledge
  • Optimize onboarding and accelerate the ramp-up time for new hires by integrating them into our dynamic culture from day one
  • Build and deliver training programs focused on raising the financial knowledge of all Sales teams to ensure consistent understanding and application across all teams
  • Lead change management efforts for key initiatives to foster widespread adoption and engagement, assessing adoption rates and employee feedback to ensure successful implementation
  • Develop playbooks detailing product positioning, marketing alignment, and system navigation for selling and adoption
  • Leverage Generative AI to gain and translate insights that will help refine and drive actionable data-driven strategies. 
  • Collaborate with the cross-functional leaders and stakeholders  applying strong sales enablement processes to help innovate and iterate on new ideas


Skills and experience we’re looking for:
  • Experience — 5+ years working in sales, sales enablement or enablement for client-facing teams Bonus points if you have experience enabling financial services or wealth management teams 
  • Learning Strategist — Deep understanding of learning principles, need analysis and various assessment techniques. You know how to address complex business challenges through targeted learning initiatives
  • Instructional Design &  Facilitation — Comfortable developing and delivering blended learning programs that engage and educate, enhancing the learning experience for all participants
  • Technology — Experience with sales platforms and familiarity with Gong.io
  • Resourcefulness — Demonstrated track record of persevering in adversity where priorities and direction can evolve quickly. Positive can-do attitude and adaptability to evolving business goals.
  • Collaboration — Excellent interpersonal and communication skills and an ability to work cross-functionally with various stakeholders
  • Flexibility — Can thrive in changing environments and is excited about contributing to innovation and bringing fresh ideas and approaches
  • Communication — Skilled in writing persuasively and communicating effectively at all levels, conveying ideas clearly and engaging meaningfully with stakeholders
  • Passion for Clients — Is incredibly passionate about our clients and our products


Why Wealthsimple?

🤑 Competitive salary with top-tier health benefits and life insurance

📈 Retirement savings matching plan using Wealthsimple Work

🌴 20 vacation days per year and unlimited sick and mental health days

📚 Up to $1,500 per year towards wellness and professional development budgets respectively 

🛫 90 days away program: Employees can work internationally in eligible countries for up to 90 days per calendar year 

🌎 A wide variety of peer and company-led Employee Resource Groups (ie. Rainbow, Women of Wealthsimple, Black @ WS)

💖 Company-wide wellness days off scheduled throughout the year


We’re a remote-first team, with over 1,000 employees coast to coast in North America. Be a part of our Canadian success story and help shape the financial future of millions — join us!


Read our Culture Manual and learn more about how we work.


DEI Statement

At Wealthsimple, we are building products for a diverse world and we need a diverse team to do that successfully. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status. 


Accessibility Statement

Wealthsimple provides an accessible candidate experience. If you need any accommodations or adjustments throughout the interview process and beyond, please let us know, and we will work with you to provide the necessary support and make reasonable accommodations to facilitate your participation. We are continuously working to improve our accessibility practices and welcome any feedback or suggestions on how we can better accommodate candidates with accessibility needs.

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CEO of Wealthsimple
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Michael Katchen
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What You Should Know About Sales Enablement Manager, Wealthsimple

At Wealthsimple, we're on the lookout for a passionate and experienced Sales Enablement Manager to join our dynamic team! In this pivotal role, you'll empower our sales teams to achieve remarkable success by equipping them with the knowledge, skills, and tools they need. We're dedicated to revolutionizing financial services for all Canadians, and as part of this mission, you'll be enhancing the capabilities of our Investment Advisor and Financial Planning teams. Your expertise will help streamline onboarding processes and develop effective training programs that ensure our teams have a solid understanding of financial products and services. You'll also leverage innovative technologies like Generative AI to refine our strategies, ensuring we remain at the forefront of the fintech industry. At Wealthsimple, collaboration is key to our success, so you'll work closely with cross-functional leaders to foster a strong sales enablement culture. If you're looking to make a significant impact and drive meaningful change in a company committed to financial transparency and accessibility, this opportunity is perfect for you!

Frequently Asked Questions (FAQs) for Sales Enablement Manager Role at Wealthsimple
What responsibilities does a Sales Enablement Manager at Wealthsimple have?

The Sales Enablement Manager at Wealthsimple is responsible for empowering sales teams by improving their knowledge, skill sets, and process adoption. This includes developing training programs, optimizing onboarding for new hires, and leading change management efforts to ensure effective implementation of sales initiatives.

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What qualifications do I need to be a Sales Enablement Manager at Wealthsimple?

To qualify for the Sales Enablement Manager position at Wealthsimple, candidates should have over 5 years of experience in sales or sales enablement, preferably within financial services. Knowledge in instructional design, strong collaboration skills, and the ability to adapt to changing business needs are also vital.

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What is the work culture like for a Sales Enablement Manager at Wealthsimple?

Working as a Sales Enablement Manager at Wealthsimple means being part of an inclusive and high-performing culture. We value collaboration, humility, and innovation. You're encouraged to bring fresh ideas to the table, all while being part of a remote-first team that spans across North America.

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How does Wealthsimple support the development of its Sales Enablement Managers?

Wealthsimple offers robust professional development opportunities, including a wellness budget of up to $1,500 annually. Sales Enablement Managers have access to various learning resources and are encouraged to engage in professional growth activities to enhance their skills and drive team success.

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What innovative technologies does Wealthsimple employ for sales enablement?

As a Sales Enablement Manager at Wealthsimple, you'd leverage cutting-edge technologies such as Generative AI to gain valuable insights and refine actionable strategies. Familiarity with sales platforms like Gong.io is also beneficial for effectively supporting our sales teams.

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Common Interview Questions for Sales Enablement Manager
How would you approach developing a training program for new sales hires?

When developing a training program for new sales hires, I would begin by assessing the specific needs and knowledge gaps of the team, followed by designing a structured curriculum that covers essential product knowledge and sales techniques. Incorporating hands-on training and mentorship would also be essential to ensure a smooth onboarding experience.

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Can you describe a successful collaboration you’ve had with a cross-functional team?

In my previous role, I collaborated with marketing and product teams to launch a new financial product. Through open communication and shared goals, we developed training resources and marketing materials that helped the sales team effectively communicate the product's value to clients.

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What strategies do you use to keep your sales team engaged during training sessions?

To keep the sales team engaged during training, I utilize interactive learning methods such as role-playing, Q&A sessions, and real-world scenarios to make the content relatable. I also encourage open discussions and feedback to foster a collaborative learning environment.

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How do you measure the success of your sales enablement initiatives?

The success of sales enablement initiatives can be measured through various metrics such as sales performance improvements, adoption rates of new processes, and feedback from sales team members. Surveys and performance assessments provide valuable insights into areas needing further refinement.

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What role does feedback play in your sales enablement strategy?

Feedback is crucial in sales enablement as it helps identify what works and what needs improvement. I regularly solicit input from sales teams to refine training materials and programs, ensuring they meet the evolving needs of the team.

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What do you think are the most important qualities for a Sales Enablement Manager?

I believe strong communication skills, adaptability, and a deep understanding of sales processes are essential qualities for a Sales Enablement Manager. Additionally, being a resourceful problem solver and possessing a passion for client success can also drive positive outcomes.

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How do you stay current with changes in the financial services industry?

Staying current in the financial services industry involves regularly reading industry publications, participating in webinars, and networking with professionals in the field. This allows me to remain informed about emerging trends and best practices in sales enablement.

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Describe a time you had to lead change management for a sales initiative.

In a recent role, I led a change management initiative to introduce a new CRM system. I organized training sessions, collaborated with stakeholders throughout the process, and gathered feedback to address any concerns, ensuring a smooth transition for the sales team.

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How do you ensure that your sales training programs are effective and relevant?

To ensure effectiveness, I base training programs on comprehensive needs analyses and continuously seek feedback from participants. I also keep content refreshed by regularly reviewing industry trends and sales strategies, ensuring that training remains relevant and applicable.

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What motivates you to excel in a Sales Enablement role?

I am motivated by the opportunity to empower sales teams and contribute to their success. Knowing that my work directly impacts sales performance and client satisfaction drives my passion for enabling others to achieve their best.

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Full-time, remote
DATE POSTED
April 3, 2025

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