Demo

Sales Enablement Analyst

Lessen
Chicago, IL Full Time
POSTED ON 1/5/2026
AVAILABLE BEFORE 2/17/2026
Lessen is the tech-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale. Lessen’s technology platform provides data-driven insights that unlock key growth opportunities for the entire real estate ecosystem—including investors, owners, managers, and service providers. The company leverages a network of over 30,000 vetted, qualified vendors (Lessen Affiliates) serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services. Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago.

Summary
The Sales Enablement Analyst will work directly under the Project Manager, Senior Lead for Process & Innovation. This role will be responsible for partnering with the Sales, Account Management, Marketing, and Solution Development teams in guiding new customers, client expansion, and renewal opportunities through Lessen’s standard Deal Process Framework, including support of solution sales and RFP responses. The Sales Enablement Analyst may also be asked to support special projects related to market research, sales technology enablement, commercial modeling and other needs as they arise.

Responsibilities
  • Supporting the Project Manager Senior Lead in developing content for new sales pursuits, existing client renewals and expansions, and other requests of the Revenue Operations Team
  • Assist the Sales Solutions team to review RFP/RFI requirements and questions; create a plan and solutions for response, across contributors and timelines
  • Ensure data integrity and maintenance of sales opportunities in Lessen’s key sales technology platforms (Salesforce & adjacent systems).
  • Top of funnel account research and targeting
  • Support Sales and Account Management teams in completing actions associated with the Deal Process.
  • Develop materials in support of existing and ramp up accounts as needed
  • Assist in the preparation of internal and client facing presentation materials
  • Ensure consistent high standards are maintained in all client-facing content and sales materials through use of templates.
  • Ensure confidentiality of internal and external data
  • Perform ad-hoc projects and other duties assigned
Role Specific Skills
  • Computer Skills: Proficient in Microsoft Word, Excel, PowerPoint, Outlook required
  • System Experience: Salesforce, Sales Navigator, Smartsheet, HubSpot or CRM experience preferred
  • Impactful communication skills: ability to support and influence sales leadership team
  • Excellent attention to detail and adherence to process
  • Comfort managing multiple projects and deadlines concurrently
  • Clarity in writing, editing, reviewing sales materials, and bid content
  • Document organization and version management control
  • Familiarity with Salesforce and other sales technology platforms

Qualifications
Minimum Qualifications
  • Bachelor’s Degree, preferably in Marketing or Communications-related fields
  • 1-3 years’ experience in content creation and project management
  • Previous experience in bid management at a facility management organization preferred

Other Relevant Qualifications
  • Experience in facilities, real estate, or property management industry preferred
Compensation:
$68,000 - 72,000 annually
Pay is determined by several compensable factors, such as qualifications, skill level, competencies, and work location.
Why Lessen:
  • Competitive compensation
  • Health, Dental, Vision, Life, Disability options
  • 401K retirement savings plan
  • Paid vacation, federal and floating holidays
  • Maternity/Paternity Pay
  • Career advancement opportunities
  • All the tools you'll need to be successful

Lessen is intentional about attracting, developing, and retaining amazing talent from diverse backgrounds. We’re looking for teammates that are enthusiastic, empathetic, curious, motivated, reliable, and will help us amplify the positive & inclusive culture we’ve been building. Lessen is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.

Salary : $68,000 - $72,000

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