Scrum Master - Engineering & Product

About Us

Stronghold Investment Management (“Stronghold,” “SIM,” or “the Firm”) is a technology-driven, vertically integrated investment manager focused on real-assets and related private markets. Stronghold seeks to deliver best-in-class risk-adjusted returns through an investment framework that features comparatively rapid transaction velocity, deep technical expertise, creative financial structuring, and objective and algorithmic decision making.

Stronghold was founded by Ryan Turner in 2016 and has deployed over $1.6 billion in capital across 10+ investment vehicles. 

Ultimately, Stronghold intends to apply its technology-intensive investment approach to a variety of specialist real assets verticals, including:

• Oil & Gas
• Renewables
• Specialty Real Estate (commercial, datacenters, marinas)
• Telecommunications and Technology Infrastructure
• Billboards and Fixtures
• Mining & other commodities
• Utilities
• Secondaries

Scrum Master - Engineering & Product

We are seeking a highly skilled Scrum Master to join our team and lead Agile transformation across our engineering and product teams. The ideal candidate will have a strong background in Agile methodologies and experience partnering closely with Product Managers to ensure alignment between business priorities, technical execution, and product outcomes. This role is critical in fostering a culture of collaboration, transparency, and continuous improvement across all cross-functional teams.

Key Responsibilities

Facilitate Scrum Ceremonies

• Lead daily stand-ups, sprint planning, sprint reviews, and retrospectives for both engineering and product teams, ensuring meetings are focused, efficient, and outcome-oriented.
• Partner with Product Managers to refine and prioritize the product backlog, ensuring clarity on goals, acceptance criteria, and delivery timelines.
• Coach team members on Agile principles and foster collaboration between product and engineering functions.
• Ensure alignment between sprint objectives and product roadmap goals.
  
  

Implement Agile Practices

• Drive adoption of Agile best practices across product and engineering, promoting consistency in workflow and delivery.
• Support Product Managers and Technical Leads in developing clear user stories, managing backlog health, and balancing technical debt vs. feature delivery.
• Act as a servant leader who removes impediments, promotes accountability, and enables both product and engineering teams to operate effectively.
• Support the organization in scaling Agile practices across multiple teams and projects.
  
  

Metric-Driven Feedback Loops

• Establish and maintain KPIs that measure not only team performance and velocity but also product delivery effectiveness, such as feature adoption, quality metrics, and time-to-market.
• Partner with Product to analyze feedback and metrics to continuously refine prioritization, delivery cadence, and product outcomes.
• Provide data-driven insights to help leadership and stakeholders understand progress toward business and product objectives.
  
  

Product Partnership & Alignment

• Collaborate closely with Product Managers to ensure sprint planning reflects strategic priorities and business goals.
• Facilitate alignment between roadmap planning, sprint execution, and release readiness.
• Support the product discovery process by enabling fast feedback loops, facilitating cross-functional discussions, and ensuring customer value remains central to sprint delivery.
• Partner with Product and Engineering leadership to continuously improve how ideas move from concept to customer delivery.
  
  

Continuous Improvement

• Identify and implement opportunities to improve collaboration between Product, Engineering, and Design.
• Encourage a culture of experimentation and innovation, empowering teams to test and iterate on both process and product ideas.
• Share best practices, lessons learned, and retrospectives across all teams to strengthen organizational agility.
  
  

Stakeholder Communication

• Act as a bridge between technical teams, Product, and business stakeholders, ensuring alignment and shared understanding of priorities and progress.
• Communicate sprint progress, key outcomes, and potential risks clearly and proactively.
• Manage stakeholder expectations, ensuring the delivery of business value that aligns with company goals and product strategy.
  
  

Qualifications

• Bachelor’s degree in Computer Science, Engineering, Product Management, or related field preferred.
• Certified Scrum Master (CSM) or equivalent Agile certification.
• 7+ years of experience as a Scrum Master or Agile Delivery Lead within technology and/or product development environments.
• Strong understanding of Agile methodologies (Scrum, Kanban, etc.) and experience applying them across multi-disciplinary teams.
• Proven experience collaborating with Product Management teams to drive roadmap execution and measurable outcomes.
• Demonstrated ability to use data and metrics to drive decisions, improvements, and product delivery quality.
• Proficiency with tools like Jira, Confluence, and product management platforms (e.g., Productboard, Aha!, or similar).
• Excellent facilitation, coaching, and leadership skills.
• Strong communication and interpersonal skills with the ability to engage effectively with technical, product, and business stakeholders.
• Ability to manage multiple priorities and adapt in a fast-paced, evolving environment.
  
  

Why work with Stronghold?

At Stronghold, we strive to create a workplace that is not only rewarding but also satisfying. We believe our employees are the driving force behind our success, and we are committed to providing them with an environment where they can thrive and reach their full potential. When you choose to work with us, you'll be joining a team of highly talented professionals who are passionate about what they do and dedicated to bringing technology expertise to our domain. We value innovation, collaboration, and a commitment to excellence, and we provide our employees with the resources and support they need to succeed. If you're looking for a challenging and fulfilling career, we invite you to apply.

Benefits

• Market-competitive compensation
• Fully paid benefits (Medical, Dental and Vision)
• HSA
• 401k + Match
• Company sponsored LTD, STD, life insurance and AD&D
• Generous PTO policy
• 20 company recognized holidays 
• Class A offices in prime locations
• Parental Leave

Equal Opportunity Employer

Stronghold Investment Management is an equal opportunity employer. We believe in creating a diverse and inclusive workforce, where individuals of all backgrounds, experiences, and perspectives can thrive. We are committed to providing equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, sexual orientation, gender identity or expression, marital status, genetic information, or any other characteristic protected by applicable laws. We encourage applicants from underrepresented groups to apply and embrace the unique contributions they can bring to our organization.