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Senior Product Manager II

Lessen is one of the fastest growing companies in the real estate services industry.  Our proprietary technology platform provides clients with portfolio dashboards, the ability to review and approve project estimates, check in on project progress in real time and pay vendors all in one place!  But we aren’t just a tech company.  We are also a property service delivery company offering renovations, turns and maintenance to residential and commercial clients.  Lessen recently acquired SMS Assist, an industry-leading facilities maintenance technology and delivery company. The new combined national footprint will serve more than 250,000 properties, facilitate approximately 2.5 million repair and maintenance orders, and complete nearly 20,000 renovation and turn projects per year.  Lessen has quickly evolved from exciting startup to valued partner, delivering scalable and turnkey property services to our clients.


Job Summary:


As a Senior Product Manager II, you will play a critical role in shaping the future of Lessen’s field service SaaS product, ensuring that it meets the needs of maintenance vendors and technicians. You will be responsible for leading key features, driving roadmap execution, and collaborating cross-functionally to enhance product stability, efficiency, and user experience. This role requires a mix of strategic thinking, customer empathy, and execution excellence to deliver a best-in-class mobile and web experience for field service professionals.


What You'll Do:


Product Strategy & Execution


- Define and execute the product roadmap for key areas within our field service SaaS platform, aligning with company goals and customer needs.

- Prioritize stability, performance, and user satisfaction, ensuring a seamless experience for field technicians and vendors.

- Own the transition and deprecation strategy for legacy product versions, ensuring a smooth migration to the new platform.


User & Market Research

- Conduct in-depth research with maintenance vendors, technicians, and industry stakeholders to uncover pain points and identify opportunities for improvement.

- Analyze market trends, competitive offerings, and emerging technologies to inform product decisions.

- Work closely with customer success and support teams to address user feedback and enhance overall satisfaction.


Cross-Functional Collaboration

- Partner with engineering, design, and data teams to deliver high-quality features that improve workflow efficiency and operational effectiveness.

- Align closely with sales and marketing teams to ensure strong go-to-market strategies and effective product messaging.

- Collaborate with the Director of Product Management to drive long-term product vision and business impact.


Metrics & Performance Tracking

- Define and monitor key product KPIs, including uptime, adoption rates, feature usage, and user satisfaction.

- Use data-driven insights to iterate and refine product capabilities, focusing on increasing technician productivity and service quality.


Customer Advocacy & Thought Leadership

- Act as a voice of the customer within the organization, ensuring that product decisions reflect real-world needs.

- Champion best practices for user onboarding, training, and change management, particularly during platform transitions.


You Should Have:


Skills & Competencies


- User-Centric Mindset: Passion for improving the daily workflows of maintenance vendors and technicians.

- Technical Fluency: Ability to work closely with engineering teams and understand complex system architectures.

- Data-driven decision-making: Strong analytical skills with experience using metrics, A/B testing, and customer feedback to guide product evolution.

- Project Management: Ability to manage multiple priorities and drive execution in an agile environment.

- Communication & Leadership: Strong storytelling and presentation skills to influence stakeholders across the company.


Experience & Background:


- 6+ years of experience in product management, with at least 3 years working on SaaS products (preferably in field service, maintenance, or operations).

- Strong understanding of mobile and web applications built for field service professionals.

- Proven track record of delivering high-impact, customer-centric product improvements in a fast-paced environment.

- Experience leading product transitions, migrations, or deprecations is a plus.


Compensation:

$115-135K

- 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. 

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Average salary estimate

$125000 / YEARLY (est.)
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$115000K
$135000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Senior Product Manager II, Lessen

Join Lessen as a Senior Product Manager II, where you’ll be at the forefront of an exciting and innovative real estate services company. Situated in Chicago, IL, Lessen is not just about cutting-edge technology; we’re about transforming property services through our unique platform that streamlines everything from project approvals to vendor payments. In this role, you will shape the future of our field service SaaS product by crafting a product roadmap that enhances stability and user experience for maintenance vendors and technicians alike. You will conduct in-depth user and market research to identify pain points and gather actionable insights to fuel our product evolution. Your collaborative spirit will shine as you partner with engineering, design, and sales teams to deliver features that significantly improve operational effectiveness. Plus, you'll be the voice of the customer within our organization, ensuring that customer feedback drives our product decision-making process. If you're passionate about using your project management skills and customer-centric mindset to make a real impact, then we’d love to chat with you about this exciting opportunity at Lessen!

Frequently Asked Questions (FAQs) for Senior Product Manager II Role at Lessen
What are the responsibilities of a Senior Product Manager II at Lessen?

As a Senior Product Manager II at Lessen, your main responsibilities include defining and executing the product roadmap for our field service SaaS platform, prioritizing product stability and user satisfaction, conducting user and market research, and collaborating cross-functionally with various teams to enhance product features. You’ll be instrumental in overseeing key product KPIs and acting as the customer advocate within the organization.

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What qualifications are required for the Senior Product Manager II position at Lessen?

To qualify for the Senior Product Manager II role at Lessen, you should have a minimum of 6 years of experience in product management, including at least 3 years focused on SaaS products, ideally within the field service or maintenance sector. Strong analytical skills, a user-centric mindset, and the ability to communicate effectively with diverse stakeholders are also essential.

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What skills are essential for a Senior Product Manager II at Lessen?

Essential skills for the Senior Product Manager II role at Lessen include a strong user-centric mindset, technical fluency to collaborate with engineering teams, data-driven decision-making skills, project management capabilities, and excellent communication and leadership skills to influence stakeholders through storytelling.

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How does Lessen support its employees in the Senior Product Manager II role?

Lessen supports its employees in the Senior Product Manager II role through competitive compensation, comprehensive benefits, professional development opportunities, and a positive workplace culture aimed at fostering growth and inclusivity. You'll also have access to tools that help you succeed in your role.

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What is the hiring process for a Senior Product Manager II at Lessen?

The hiring process for a Senior Product Manager II at Lessen generally involves an application review, followed by a series of interviews where candidates are assessed on their product management skills, cultural fit, and technical knowledge. It's an opportunity for both the company and potential employees to determine mutual compatibility.

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Common Interview Questions for Senior Product Manager II
Can you describe your approach to defining a product roadmap?

When defining a product roadmap, it's crucial to align with company goals while keeping user needs in mind. Start by conducting market research and user interviews to gather data on pain points. Prioritizing features that enhance user satisfaction and product stability should be your guiding principle.

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How do you handle conflicting priorities from different stakeholders?

Handling conflicting priorities requires clear communication and negotiation. I advocate for the customer while considering each stakeholder's needs. By organizing discussions, assessing the impact of each request, and using data to support decisions, I work to reach a consensus that aligns with overall product strategy.

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Describe a successful product launch you led.

In a successful product launch I led, I focused on user research and used iterative feedback to refine our approach. Collaborating across teams was key, and we launched with a robust marketing strategy that highlighted user benefits. Post-launch, careful monitoring of KPIs helped us quickly address any initial issues.

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What methods do you use to evaluate product success?

To evaluate product success, I track key performance indicators (KPIs) like user adoption rates, feature usage, and customer satisfaction scores. Analyzing this data allows me to identify areas for improvement and iterate on the product effectively.

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How do you gather and incorporate user feedback in your product management process?

I gather user feedback through various channels like surveys, interviews, and usability testing. Incorporating this feedback involves analyzing trends and pain points, followed by prioritizing actionable insights in the product backlog to ensure we address real user needs.

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What experience do you have with agile product management?

I have extensive experience with agile product management, including working in sprints and adapting to rapid changes. Regular team stand-ups and retrospectives have helped me foster collaboration and keep the team aligned on our goals throughout the product lifecycle.

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How do you ensure the technical feasibility of your product ideas?

Ensuring technical feasibility begins with early collaboration with engineering teams. I consult with them during the ideation phase and rely on their expertise to assess the technical challenges and constraints, enabling secure planning and execution of product features.

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How do you stay updated with industry trends and technologies?

I stay updated by subscribing to industry publications, participating in webinars, and being active in professional product management communities. Networking with other professionals also provides valuable insights into emerging trends and technologies that can influence our product direction.

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Can you provide an example of how you've driven cross-functional collaboration?

In a past role, I initiated cross-functional workshops that brought together stakeholders from engineering, sales, and customer support. These sessions encouraged open dialogue about product features and led to collaborative solutions that were beneficial for both our team and customers.

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What do you think sets a great product manager apart from a good one?

A great product manager combines strong analytical skills with emotional intelligence. They not only rely on data but also understand their users’ emotions, allowing them to build empathy-driven products that truly resonate with customers while achieving business objectives.

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At Lessen, we are on a mission to help service professionals “lessen” the burden of doing great work and property owners “lessen” the burden of servicing their properties. We are building a world-class technology platform that is fundamentally cha...

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April 5, 2025

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