Trade Specialist II

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Chicago, IL, USA
Hybrid
70K-80K Annually
Cloud • Real Estate • Software • PropTech
Help us revolutionize real estate services.
The Role
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. 

Job Summary
 
The HVAC Trade Specialist II plays an integral role in customer and vendor support to a specific client base. This role is responsible for implementing and maintaining client and associate relationships, while serving as a specific trade related SME for complex issues and queries, proactively resolving their daily challenges.

What You'll Do

  • Build and maintain professional relationships with clients and vendors to gain an understanding of their operational needs in a specific trade related area, assists in the development and implementation of solutions to meet those needs
  • Review vendor quotes on behalf of client to ensure scope and pricing of HVAC/Refrigeration work is appropriate
  • Develop and coordinate client and internal initiatives and special projects
  • Serve as a technical and subject matter expert resource for HVAC/Refrigeration and leadership
  • Serve as a key point of contact for internal and external clients; resolving issues with vendors as necessary
  • Proactively resolve vendor and client issues; drive all issues towards resolution and escalates on a timely basis only when necessary
  • Provide support to Trade Representative as required
  • Foster a positive work environment and collaborate effectively with all stakeholders
  • Ensure confidentiality of internal and external data
  • Perform ad-hoc projects and other duties as assigned
  • Maintain CPD and awareness of trade / industry developments
  • Seek opportunities for continuous process improvement

What You'll Need

  • Computer Skills: Intermediate proficiencies in: Microsoft Word, Excel, PowerPoint, Outlook preferred
  • SME in HVAC/Refrigeration trade
  • Relevant HVAC/Refrigeration trade qualification
  • 3 – 4 years of experience in relevant field
  • Experience working in an FM, retail, buildings environment
  • Demonstrable experience of solving complex trade related technical issues
  • Bachelor’s Degree preferred
  • #IND1

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. 

What the Team is Saying

Jay Payne
Kirby Pumper
Maya Shea
Jay McKee
Jennifer Gordon
Trevon

Lessen LLC Compensation & Benefits Highlights

  • Leave & Time Off Breadth Flexible or 'unlimited' PTO and paid parental leave are highlighted, with volunteer time also appearing in the package. Feedback suggests time‑off options are a meaningful element, particularly for exempt roles.
  • Healthcare Strength Medical, dental, and vision coverage are paired with on‑demand counseling/EAP and wellness resources. Feedback suggests the core health offering is solid and broadly aligned with market norms.
  • Wellbeing & Lifestyle Benefits Perks include pre‑tax commuter options, pet insurance, and wellness programming, with some roles noting home‑office stipends. Feedback suggests these extras add breadth beyond the basics.

Lessen LLC Insights

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The Company
HQ: Scottsdale, Arizona
713 Employees
Year Founded: 1999

What We Do

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. To learn more, visit Lessen.com.

Why Work With Us

We make caring for and improving properties simpler, faster, better. Powered by tech and perfected by people, we deliver best-in-class, transformational solutions to deliver assets to market faster, keep businesses up and running, and improve customer and resident experiences. We're property services, simplified.

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Lessen LLC Teams

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About our Teams

Lessen LLC Offices

Hybrid Workspace

Employees engage in a combination of remote and on-site work.

At Lessen, managers decide how teams work best—office, home, or hybrid. We value flexibility, connection, and outcomes, investing in tools that keep everyone aligned and focused on delivering great results together.

Typical time on-site: 3 days a week
HQScottsdale, AZ
Chicago, IL
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