Lessen Jobs in Chicago, IL (NOW HIRING)

Positioning & Messaging 

• Develop and maintain product and service-line messaging for assigned Lessen products, services, audiences, and GTM motions. 

• Translate complex platform capabilities, managed execution models, AI-enabled workflows, service-line differentiators, and operational proof points into clear business outcomes. 

• Support messaging development for residential, commercial, vendor, and client audiences. 

• Create and update messaging frameworks, product narratives, persona messaging, proof points, value propositions, FAQs, and positioning guardrails. 

• Ensure product and service-line messaging is consistent across sales decks, website copy, campaigns, collateral, launch materials, and internal enablement. 

• Partner with the Director of Product Marketing to keep each Lessen product and service offering clearly differentiated within the broader platform ecosystem. 

Go-to-Market & Launch Support 

• Support go-to-market planning for product launches, feature releases, service expansions, packaging updates, and major commercial initiatives. 

• Build launch materials, including internal briefs, messaging docs, sales talking points, FAQs, enablement decks, and customer-facing collateral. 

• Partner with Product to understand roadmap priorities, release details, product capabilities, customer impact, and readiness requirements. 

• Partner with Demand Generation and Content teams to ensure campaigns are grounded in accurate product messaging and buyer needs. 

• Help create repeatable launch processes, templates, and documentation standards. 

• Track launch readiness across key stakeholders and ensure sales and customer-facing teams have the materials they need before launch. 

Sales Enablement & Commercial Support 

• Build and maintain sales enablement materials, including pitch decks, battlecards, objection handling guides, one-pagers, talk tracks, product FAQs, competitive comparisons, and ROI narratives. 

• Partner with Sales leadership and frontline sellers to understand where messaging, tools, or competitive resources are needed. 

• Support strategic deals by helping tailor product messaging, proof points, and competitive positioning for specific customer needs. 

• Develop vertical- and segment-specific materials for priority markets across residential and commercial real estate. 

• Ensure enablement materials are practical, easy to use, and aligned to how sales teams actually sell. 

• Gather feedback from Sales and Customer Success to continuously improve messaging and collateral. 

Competitive & Market Intelligence 

• Research competitors, market trends, buyer needs, and category shifts across property services, property operations, field service, facilities management, procurement, AI-enabled operations, and related technology markets. 

• Create and update competitive battlecards, positioning briefs, objection responses, and internal reference materials. 

• Monitor competitor messaging, product launches, pricing signals, customer proof points, and market claims. 

• Help Sales understand where Lessen wins, where competitors are strong, and how to frame differentiation clearly and credibly. 

• Turn research into actionable insights for Product, Sales, Marketing, and leadership. 

Product, Service Line & Buyer Expertise 

• Develop deep knowledge of Lessen's products, service lines, buyers, users, competitors, and market categories. 

• Build working fluency across the full Lessen ecosystem, including Residential Services, Commercial Services, ONE by Lessen, Lessen360, Lessen Pro, Marketplace, Aiden, and emerging offerings. 

• Understand how Lessen's product and service offerings fit together across residential, commercial, vendor, and client audiences. 

• Support messaging and enablement needs across both named products and service-line GTM motions, including residential property services, commercial property services, managed execution, self-managed platform models, field execution, procurement, and embedded intelligence. 

• Understand how each offering fits into Lessen's broader platform story and where each one is most relevant by audience, segment, and sales motion. 

• Support product marketing needs across multiple products, service lines, and audiences, with the expectation that ownership may narrow over time into one or two primary areas or GTM motions. 

• Understand the needs of executive buyers, operations leaders, maintenance leaders, facilities leaders, vendor owners, technicians, finance stakeholders, and day-to-day platform users. 

• Partner with Product, Sales, Customer Success, Operations, and Marketing to gather customer insights, sales feedback, win/loss learnings, and voice-of-customer themes. 

• Help connect product and service capabilities to buyer pain points, operational outcomes, and measurable business value. 

• Support customer proof development, including case studies, testimonials, success metrics, and use-case narratives. 

Content & Cross-Functional Execution 

• Write clear, polished, product-informed content for internal and external audiences. 

• Support website updates, campaign messaging, product pages, landing pages, sales scripts, event messaging, and thought leadership content as needed. 

• Collaborate with Design, Content, Demand Generation, Product, Sales, Customer Success, Operations, and Marketing to bring product stories to life. 

• Maintain organized documentation and ensure materials are easy for internal teams to find, understand, and reuse. 

• Use LLMs and AI tools thoughtfully to work more efficiently across research, message testing, first-draft development, synthesis, competitive review, and content repurposing while maintaining accuracy, quality, confidentiality, and appropriate human review. 

• Perform other product marketing, sales enablement, and go-to-market projects as assigned.