📌 Core Information
🔹 Job Title: Senior Content Strategist
🔹 Company: Lessen
🔹 Location: Chicago, IL
🔹 Job Type: Full Time
🔹 Category: Marketing & Communications
🔹 Date Posted: 2025-05-15
🔹 Experience Level: 10+ years
🔹 Remote Status: On-site
🚀 Job Overview
Key aspects of this role include:
- Overseeing content creation and curation for all customer-facing communications across multiple channels
- Developing and executing campaigns across social, email, digital, and print channels
- Creating sales enablement tools such as pitch decks, case studies, and white papers
- Managing an internal content development team and industry content contributors
- Measuring content performance and driving audience engagement
ASSUMPTION: This role requires a strategic mindset, strong leadership skills, and a deep understanding of digital content marketing.
📋 Key Responsibilities
✅ Oversee the content creation and curation for all customer-facing communications in all channels
✅ Help ideate, develop, and execute campaigns across social, email, digital, and print channels
✅ Create new sales enablement tools: pitch decks, case studies, white papers, collateral, etc.
✅ Oversee the creation and maintenance of editorial calendars, style guides, metadata frameworks used for the creation, curation, and governance of content, conducting regular audits
✅ Lead an internal content development team; find and manage industry content contributors for additional content creation; foster creation of user-generated content (UGC) as determined
✅ Identify and seize opportunities to grow audience and engagement across platforms, contributing to measurable lead generation, collaborate with digital team on earned, owned, and paid media
✅ Support growing social media program and online reputation management. Ideate and execute social component of campaigns and events in collaboration with the marketing and digital team
✅ Develop content strategy and support speaker/attendee acquisition for virtual and in-person events such as conferences, trade shows, webinars, podcasts, sponsorships, and more
✅ Oversee and work with appropriate teams to support new digital efforts, such as mobile and online initiatives, monitor and drive audience engagement in partnership with digital team
✅ Build relationships with outside agency for press and media; work toward creative placement and pitch story ideas as it fits into larger business/brand strategy; integrate press mentions into content marketing execution
✅ Measure the impact of the content created and understand how it performs against goals. Use our marketing automation platform, Salesforce, to oversee marketing initiatives. Show ROI through creative reporting and analysis on a regular basis.
✅ Improve content awareness through SEO optimization
✅ Ensure confidentiality of internal and external data
✅ Perform ad-hoc projects and other duties as assigned
ASSUMPTION: This role requires a high level of organization, strong project management skills, and the ability to work collaboratively with various teams.
🎯 Required Qualifications
Education: Bachelor’s degree in marketing, communications, journalism, writing, or equivalent
Experience: 10 or more years of professional copywriting, editing, and/or digital content creation with 5 or more years spent in channel content strategy development and managing a team
Required Skills:
- Advanced editing and proofing skills
- Command of writing content specifically optimized for digital channels utilizing best practices
- Computer Skills: Experience with Webflow, Google Analytics, and the top social channels
- Understanding of content needs for distribution via different channels (email, social, paid, direct mail, SEO, etc.)
- Experience with Content Management Systems (CMS)
- Proficient in all people management processes, including recruitment, performance management and reward
- Proficient in building, growing and developing a team; including department structure design and resourcing
- Proficient in coaching and developing individual team members to reach their potential
- Proficient in engaging a team through communication, processes, personal impact and influence
Preferred Skills:
- Experience with Salesforce Marketing Cloud
ASSUMPTION: Candidates should have a strong portfolio showcasing their content strategy and management skills, as well as examples of their writing and editing work.
💰 Compensation & Benefits
Salary Range: $80,000 - $95,000 annually
Benefits:
- Health, Dental, Vision, Life, Disability options
- 401K retirement savings plan
- Paid vacation, federal and floating holidays
- Maternity/Paternity Pay
- Career advancement opportunities
Working Hours: 40 hours per week
ASSUMPTION: The salary range provided is based on industry standards for a senior content strategist role in the Chicago area.
📌 Applicant Insights
🔍 Company Context
Industry: Facilities Services. Lessen is a technology-enabled, end-to-end property service provider that is transforming how commercial and residential real estate services are delivered and managed at scale.
Company Size: 1,001-5,000 employees. Lessen offers a large and diverse work environment with ample opportunities for career growth and development.
Founded: 1999. Lessen has a long history in the facilities services industry and a strong track record of success.
Company Description:
- Lessen leverages a network of over 30,000 vetted, qualified vendors serving clients with over 1 million properties and completing more than 3.5 million work orders annually across an expanding range of services.
- The company'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.
- Lessen, LLC is a venture-backed, privately held company with offices in Scottsdale and Chicago.
Company Specialties:
- Facility Management
- Snow and Ice Management
- HVAC
- Landscaping
- Reactive and Preventive Maintenance
- Capital Projects
- Floor Care
- One by SMS Assist Proprietary Technology
- A Vetted Affiliate Network of 20,000+
- A 24/7 Customer Service Organization
Company Website: http://lessen.com
ASSUMPTION: Lessen's extensive network and proprietary technology make it a strong player in the facilities services industry.
📊 Role Analysis
Career Level: Senior-level role with significant strategic and management responsibilities.
Reporting Structure: The Senior Content Strategist will report directly to the VP of Marketing and will oversee an internal content development team.
Work Arrangement: On-site, full-time position with the opportunity for remote work as needed.
Growth Opportunities:
- Potential to advance to a VP or Director-level role within the marketing department
- Opportunities to expand the content team and take on additional responsibilities
- Chance to work on high-impact projects that drive business growth and improve customer experience
ASSUMPTION: This role offers significant growth potential for the right candidate with strong leadership and strategic skills.
🌍 Location & Work Environment
Office Type: Corporate office environment with a collaborative and dynamic team.
Office Location(s): 130 E Randolph St, Suite 200, Chicago, IL 60601, US
Geographic Context:
- Chicago is a major metropolitan area with a diverse economy and a thriving job market
- The office is located in the heart of downtown Chicago, offering easy access to public transportation and numerous amenities
- Chicago is known for its vibrant cultural scene, including world-class museums, theaters, and music venues
Work Schedule: Standard business hours with flexibility for remote work as needed.
ASSUMPTION: The downtown Chicago location offers a convenient and vibrant work environment with ample opportunities for professional growth and development.
💼 Interview & Application Insights
Typical Process:
- Online application and resume submission
- Phone or video screen with the HR department
- In-person or virtual interview with the hiring manager and/or team members
- Final interview with the VP of Marketing
- Background check and offer extension
Key Assessment Areas:
- Content strategy and management skills
- Writing and editing abilities
- Project management and team leadership skills
- Understanding of digital content marketing and SEO optimization
- Alignment with Lessen's company culture and values
Application Tips:
- Tailor your resume and cover letter to highlight your relevant content strategy and management experience
- Include examples of your writing and editing work, as well as any content strategy projects you've led
- Prepare for behavioral interview questions that focus on your leadership, project management, and problem-solving skills
- Research Lessen's company culture and values to demonstrate your fit with the organization
ATS Keywords: Content strategy, content management, digital marketing, SEO optimization, team leadership, project management, campaign development, social media management, content creation, editorial calendar, brand voice, press relations
ASSUMPTION: Lessen's hiring process is designed to assess candidates' strategic thinking, leadership, and content creation skills, as well as their cultural fit with the organization.
🛠️ Tools & Technologies
- Webflow
- Google Analytics
- Social media platforms (e.g., LinkedIn, Twitter, Facebook)
- Content Management Systems (CMS)
- Salesforce Marketing Cloud
ASSUMPTION: Familiarity with these tools and technologies is essential for success in this role.
👔 Cultural Fit Considerations
Company Values:
- Customer-centric
- Innovative
- Collaborative
- Accountable
- Empowering
Work Style:
- Dynamic and fast-paced
- Collaborative and team-oriented
- Data-driven and results-focused
- Adaptable and responsive to change
- Customer-focused and customer-obsessed
Self-Assessment Questions:
- How do you ensure that your content strategy aligns with Lessen's customer-centric approach?
- Can you provide an example of a time when you had to adapt your content strategy in response to changing customer needs or market conditions?
- How do you foster a collaborative and inclusive work environment that empowers your team members to reach their full potential?
ASSUMPTION: Lessen's company culture values collaboration, innovation, and a customer-centric approach, making it an ideal fit for candidates with strong leadership, strategic, and communication skills.
⚠️ Potential Challenges
- Managing a large volume of content creation and curation across multiple channels
- Balancing strategic content planning with day-to-day tactical execution
- Working with a diverse range of stakeholders, including sales, product, and affiliate relations teams
- Keeping up with the latest trends and best practices in digital content marketing
- Ensuring consistent brand voice and messaging across all customer-facing communications
ASSUMPTION: These challenges require strong project management, leadership, and communication skills, as well as the ability to work collaboratively with diverse teams.
📈 Similar Roles Comparison
- Unlike other content strategy roles, this position requires a high level of management and leadership skills, as well as experience in people management processes
- This role offers a unique opportunity to work in the facilities services industry, which is a dynamic and growing sector with a wide range of content marketing opportunities
- Career progression in this role could lead to advancement to a VP or Director-level position within the marketing department, with potential to expand the content team and take on additional responsibilities
ASSUMPTION: This role offers a unique blend of strategic, management, and creative responsibilities, making it an attractive opportunity for candidates with a strong background in content strategy and management.
📝 Sample Projects
- Developing and executing a comprehensive content marketing strategy for a major product launch
- Managing a team to create and curate a large-scale content campaign for a major industry event
- Conducting a content audit and overhaul of a company's website and digital presence
ASSUMPTION: These projects demonstrate the strategic, management, and creative skills required for success in this role.
❓ Key Questions to Ask During Interview
- Can you describe the current content marketing landscape at Lessen and how this role fits into the overall marketing strategy?
- How does Lessen support the professional development and growth of its content team members?
- What are the biggest content marketing challenges facing Lessen in the next 12-24 months, and how does this role address those challenges?
- How does Lessen measure the success of its content marketing efforts, and how will this role contribute to those metrics?
- What are the key priorities for this role in the first 30-60-90 days, and how will my performance be evaluated during this onboarding period?
ASSUMPTION: These questions demonstrate your interest in the role and your understanding of the strategic and management responsibilities required for success.
📌 Next Steps for Applicants
To apply for this position:
- Submit your application through http://lessen.com/careers
- Tailor your resume and cover letter to highlight your relevant content strategy and management experience, including any projects or initiatives you've led that demonstrate your strategic thinking, leadership, and project management skills
- Prepare for behavioral interview questions that focus on your leadership, project management, and problem-solving skills, as well as your ability to work collaboratively with diverse teams
- Research Lessen's company culture and values to demonstrate your fit with the organization
- Follow up with the hiring manager one week after submitting your application to express your continued interest in the role
⚠️ This job description contains AI-assisted information. Details should be verified directly with the employer before making decisions.
