Full-Time

Sales Director

Commercial

Posted on 5/14/2025

Lessen

Lessen

1,001-5,000 employees

Property services marketplace and SaaS platform

No salary listed

Scottsdale, AZ, USA

Hybrid

Category
Sales & Account Management (2)
,
Requirements
  • Bachelor’s degree required
  • At least 5 years of sales experience and a minimum of 3 years of complex sales to executives in large organizations, ideally in technology or facility services required
  • Strong business development process and sales pipeline orientation, including effective use of CRM systems such as Salesforce.com
  • Basic knowledge of sales process, methodology and data required
Responsibilities
  • Meet or exceed annual sales quota.
  • Excel at the introduction and positioning of the Lessen value proposition at various levels of prospect organizations.
  • Compel the C-Suite, procurement, or business owners to prioritize a fully outsourced solution or “a la carte” solution that generates revenue from base business organic growth, as well as from referrals.
  • Create prospecting activity that exceed monthly quota for activity and appointments.
  • Develop and maintain a 4X rolling annual pipeline.
  • Provide forecasting predictability and accuracy.
  • Contribute to the development and effectiveness of inside sales resources.
  • Maintain and foster existing customer relationships via face-to-face appointments, phone conversations, and emails.
  • Potentially maintain ongoing communication with customers to understand their needs and provide solutions.
  • Demonstrate solution and value proposition and deal with customer issues, questions, and uncertainties.
  • Potentially identify and deliver on any opportunities to increase Lessen's suite of offerings to existing customers.
  • Potentially maintain relationships with the current install base and looks to expand services in each account
  • Maintain up-to-date, detailed customer knowledge and industry data; serves as an active member of groups and associations related to the industry and relevant customers.
  • Update all sales activity, initiatives by category, customer and status in Salesforce.com
  • Use appropriate selling strategies and techniques to engage clients at all stages of the pipeline, and identifies and addresses any weaknesses in the strategy
  • Operate within Financial, Legal, and Ethical Policies; responsible for driving the growth of revenue and profit originating from the Sales department; manages the Sales Profit and Loss statement
  • Participate and influence multiple projects at a given time, ensuring adherence to process, monitor progress, mentor project leads, and direct implementations to successful conclusion
  • Domestic travel required up to 50%.
  • Foster a positive team environment.
  • Ensure confidentiality of internal and external data.
  • Perform ad-hoc projects and other duties as assigned.

Lessen provides a technology-powered end-to-end platform that connects property owners with a network of verified professionals for maintenance, repairs, and renovations. Its marketplace plus SaaS tools manage bidding, scheduling, payment, and quality control across portfolios. Unlike general property marketplaces, Lessen targets institutional investors, property managers, and real estate owners, offering integrated procurement and portfolio management. Its goal is to simplify and scale property maintenance and renovations, delivering transparent, auditable workflows while generating revenue from transaction fees and software subscriptions.

Company Size

1,001-5,000

Company Stage

Late Stage VC

Total Funding

$1.2B

Headquarters

Scottsdale, Arizona

Founded

2019

Simplify Jobs

Simplify's Take

What believers are saying

  • Lessen handles over 3.5 million work orders annually across 1 million properties.
  • Lessen Advantage Marketplace increases vendor stickiness through insurance, financing, and materials discounts.
  • Expansion into scheduled services and capital projects broadens wallet share materially.

What critics are saying

  • Yardi and HappyCo can disintermediate Lessen by bundling native maintenance workflows.
  • Vendor quality slippage across 30,000 contractors will erode trust and divert volume.
  • Integration of Blue Skyre IBE can disrupt operations and trigger customer churn.

What makes Lessen unique

  • Lessen combines work-order software with a 30,000-vendor service network.
  • Its platform spans maintenance, repairs, renovations, and make-ready workflows.
  • Yardi and HappyCo integrations embed Lessen inside property managers' daily systems.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

Disability Insurance

401(k) Retirement Plan

Paid Vacation

Parental Leave

Career Advancement Opportunities

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

-1%
France Media
Mar 5th, 2025
Lessen Opens New 76,932 SF Office in Downtown Chicago

Lessen opens new 76,932 SF office in downtown Chicago.

Business Wire
Jan 6th, 2025
Lessen Announces Integration with Yardi, Offering Seamless Access to On-Demand Services and Maintenance Solutions

Lessen360(TM), a cloud-based platform purpose-built for centralized maintenance operations, is now fully integrated with Yardi Voyager, enabling real-time synchronization of work orders and make-readies between the platforms.

Business Wire
Apr 2nd, 2024
Lessen Launches Innovative Purchasing Marketplace For Vendors

SCOTTSDALE, Ariz.--(BUSINESS WIRE)--Lessen, the premier tech-enabled, end-to-end solution for outsourced real estate property services, today announced the launch of the “Lessen Advantage Marketplace.” This centralized, dynamic hub allows vendors who are part of the Lessen Advantage™ community to enjoy access to a diverse range of products and services geared toward maximizing efficiency and fostering growth. The Marketplace includes access to preferred rates on insurance and bank financing, as well as access to thousands of products and materials through One Source, an integrated e-commerce purchasing hub. On average, users will benefit from savings of over 18% compared to prevailing retail prices. "We want to help our vendor community to save time and money on all of their projects,” said Lessen founder and CEO Jay McKee. "Our marketplace is another step forward in our goal to transform how property services are managed.”

Business Wire
Nov 30th, 2023
Real Estate Marketplace Platform Lessen Closes $170 Million Series B Funding Round

Lessen announces that it has closed a $170 million Series B funding round along with a company valuation of more than $1 billion.

The Business Journals
Sep 27th, 2023
First look: Scottsdale-based proptech firm expands into new amenity-filled headquarters

Scottsdale-based Lessen Inc. will stay within the city but has moved offices from 4021 N. 75th Street into the Portales Corporate Center I at 4800 N. Scottsdale Road.

INACTIVE