Sales Enablement and Effectiveness Lead

Remote Full TimeToronto, ON, CanadaInsightly

Insightly, the new breed of CRM, helps modern businesses of all sizes build lifelong customer relationships and grow faster than ever before. Insightly’s out of the box capabilities allow you to tailor each user’s experience for every customer facing role. It is easy to use, easy to set up, highly customizable to your industry, and offers fast time to value at a low total cost of ownership. With more than 1.5 million users and over 25,000 companies worldwide, Insightly is the world’s most popular CRM software for Google and Office 365 users.

Founded in 2009 and based in San Francisco, Insightly is backed by $50 million in funding from leading venture capital firms: Emergence Capital Partners, Cloud Apps Capital Partners, Scott Bommer and Sozo Ventures.

Sales Enablement and Effectiveness Lead

Insightly is looking for a great Sales Enablement and Effectiveness Lead to create and deliver world-class enablement solutions for our sales team. You will be responsible for the development, delivery, adoption, and measurement of sales enablement programs and initiatives that supports the buying and selling processes at all stages, from lead generation through win/loss.With this career opportunity, you will leverage your skills in sales, curriculum design and content development to help build, maintain and deliver sales training for a rapidly growing sales organization.

Key Responsibilities Include

  • Design and deliver a broad range of sales enablement programs designed to reduce ramp time and increase performance to sales quotas
  • Ensure new sales account executives and sales engineers are proficient in Insightly product knowledge, value proposition, messaging, competitive landscape and the Insightly sales process
  • Document sales processes from lead mgmt., opportunity mgmt., account management and all in between
  • Develop sales team working knowledge of relevant sales tools and processes
  • Drive proactive focus on daily usability and performance of the Insightly sales tech stack
  • Develop course facilitation and instructor guides/ students guides
  • Collaborate with content creators across the company to identify the best content possible to accelerate the success of the audience


  • 2+ years SaaS sales experience preferred
  • 3+ years of experience building and delivering effective sales enablement programs that have a demonstrable impact on revenue generation
  • Versed in sales process (CRM), sales value messaging (Challenger, Command of the Message, Miller-Heiman) and sales methodology (MEDDICC)
  • Proficiency with developing e-learning courseware using Adobe Captivate, Articulate, or other best of breed authoring tool
  • Proficiency with sales productivity tools such as Gong, SalesLoft, and SalesNavigator
  • Skilled in the creation, implementation, and validation of assessments to measure the effectiveness of training to achieve business priorities and significantly impact results
  • Strong communication and presentation skills
  • Current on instructional innovation and technology

What else?

  • Career: We offer a well rounded total rewards package including equity for all employees, 401k, career learning & growth opportunities, and comprehensive employer-sponsored health plans.
  • Work-life balance: We offer a generous flexible time off policy in addition to paid company holidays.
  • A company that cares! Insightly is now a 100% remote first company, which includes all of the benefits we provide for our employees to best adapt to the challenges and needs of a digital and dispersed workforce:
    • Full IT set up for your home work station (laptop, monitor, keyboard, mouse, monitor stand)
    • $250 one-time Ergonomics Stipend for all employees to set up their home office for success and comfort
    • $50 per month remote work stipend to help you with your remote work needs
    • Monthly virtual and instructor-led meditation sessions
    • Annual membership to Peloton fitness app
    • Monthly company newsletters, professional speakers, and more!
    • Virtual team and company events to keep the party going
  • Culture and Values: Diversity, Inclusion, and Support for all employees is vital to Insightly. To do so we have fantastic initiatives such as:
    • Company wide Women in Tech group, which focuses on having female speakers from all backgrounds come and have “fireside chats” with the company on their careers, backgrounds, advice, etc.
    • Women in Sales support group, which focuses on professional development, community, and career advancement
    • Continual company-wide Diversity and Inclusion training with expert speakers and instructors
    • Company matched donations to support Black and civil rights charities such as NAACP, BLM, ACLU, George Floyd Memorial Fund, Compassion Oakland, Asian Americans Advancing Justice, and more!

Our Mission

To empower companies to build lasting relationships with their customers.

Core Values

  • We play as a team.
  • We are ambitious and think big.
  • We strive to make customers happy.
  • We build with simplicity not complexity.

Insightly is on a significant growth trajectory with a solid track record and reputable investors. We have concluded a Series C financing round and are backed by Emergence Capital Partners, Cloud Apps Management LC, Sozo Ventures, and TrueBridge Capital Partners.

Insightly is an Equal Employment Opportunity and Affirmative Action Employer and provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, martial status, or any other characteristic protected by federal, state, or local laws.

Insightly is committed to offering an inclusive and accessible experience for all job seekers, including individuals with disabilities. If you need a reasonable accommodation to search for a job opening, apply for a position, or participate in the interview process, please contact [email protected] and describe the specific accommodation requested for a disability-related limitation. A request for an accommodation will be responded to, but non-disability related requests, such as following up on an application or submitting application materials, will not receive a response.

When you apply to a job on this site, the personal data contained in your application will be collected by Insightly, Inc. (“Controller”), which is located at 58 West Portal Ave PMB 716 San Francisco, CA 94127 and can be contacted by emailing [email protected] . Your personal data will be processed for the purposes of managing Controller’s recruitment related activities, which include setting up and conducting interviews and tests for applicants, evaluating and assessing the results thereto, and as is otherwise needed in the recruitment and hiring processes. Such processing is legally permissible under Art. 6(1)(f) of Regulation (EU) 2016/679 (General Data Protection Regulation) as necessary for the purposes of the legitimate interests pursued by the Controller, which are the solicitation, evaluation, and selection of applicants for employment.

Your personal data will be shared with Greenhouse Software, Inc., a cloud services provider located in the United States of America and engaged by Controller to help manage its recruitment and hiring process on Controller’s behalf. Accordingly, if you are located outside of the United States, your personal data will be transferred to the United States once you submit it through this site. Because the European Union Commission has determined that United States data privacy laws do not ensure an adequate level of protection for personal data collected from EU data subjects, the transfer will be subject to appropriate additional safeguards under [either the standard contractual clauses or the Privacy Shield]. You can obtain a copy of the standard contractual clauses by contacting us at [email protected] .

Your personal data will be retained by Controller as long as Controller determines it is necessary to evaluate your application for employment. Under the GDPR, you have the right to request access to your personal data, to request that your personal data be rectified or erased, and to request that processing of your personal data be restricted. You also have to right to data portability. In addition, you may lodge a complaint with an EU supervisory authority.

  • This position has been filled

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