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VP, Engineering

Forward Financing is a Boston-based financial technology company with an operational hub in the Dominican Republic, providing fast, flexible working capital to US small businesses that have been underserved by traditional financing options. It is our mission to build a world-class fintech company so our customers and our people can reach their full potential. Forward has been recognized as a Best Place to Work by the Boston Business Journal and Built In Boston and is certified as a Great Place to Work.® We’re investing in our employees, technology, and customer experience – with long-term success in mind every step of the way.

As Vice President of Engineering, you will have a strong background in software development, demonstrating expertise in designing and delivering high-quality solutions. A key focus will be fostering a collaborative, innovative, and results-driven engineering culture that inspires teams to excel. This leader must have the ability to effectively manage and guide multiple engineering teams, ensuring alignment across diverse projects and priorities. They will partner closely with business unit leaders and product teams to develop impactful and reliable software solutions that align with organizational goals. A deep understanding of business objectives is essential, along with the ability to leverage technology effectively to achieve strategic outcomes.

In this role you will:

  • Serve as a senior leader within the broader technology organization, playing a key role in shaping its strategy and direction.
  • Oversee multiple engineering teams, working in close collaboration with the Chief Technology Officer, Product Management, and TechOps teams to deliver a unified vision and roadmap.
  • Partner with leaders across the business to understand their needs, set clear expectations, provide technical thought leadership, and regularly address challenges and opportunities.
  • Demonstrate a strong bias for action mindset, driving initiatives forward with urgency and a focus on delivering impactful results in a timely manner
  • Inspire and empower engineering talent within your teams, fostering professional growth and a culture of excellence.
  • Drive a focus on scalability, efficiency, reliability, and the use of meaningful metrics to measure and enhance team performance.
  • Actively contribute to strategic planning and review processes, preparing and presenting updates, opportunities, and challenges in forums such as quarterly and annual planning, while soliciting feedback from executive leaders.
  • Make key architectural decisions by collaborating with senior technical contributors to define and execute technical roadmaps that align with organizational goals.
  • Recruit, develop, and mentor engineering leaders and team members, ensuring the organization remains equipped with top-tier talent.

Additionally as VP of Engineering, you will:

  • Champion a strong engineering culture that values innovation, accountability, and customer-centric problem-solving.
  • Lead initiatives to modernize and scale systems, ensuring alignment with evolving business and technical requirements.
  • Drive strategic make-buy-build decisions, assessing when to leverage external solutions, build in-house capabilities, or integrate a hybrid approach to achieve business objectives efficiently.
  • Leverage global technology resources effectively, tapping into talent and capabilities across geographies to optimize costs and productivity while maintaining a high standard of quality.
  • Foster a culture of accountability by setting clear expectations, establishing measurable goals, and ensuring that team members take ownership of their work and outcomes.
  • Identify and implement emerging technologies and best practices to maintain a competitive edge.
  • Act as a key advocate for engineering, articulating its value and impact to stakeholders at all levels of the organization.
  • Collaborate with cross-functional teams to drive alignment on priorities, timelines, and deliverables for key business initiatives.
  • Ensure the engineering organization is structured and resourced to support long-term business goals and innovation strategies.

Requirements:

(Even if you don’t check every box, but see yourself contributing, please apply.)

  • At least 10 years of experience in software engineering leadership, including 5+ years managing multiple teams and mentoring other engineering managers.
  • Experience in the consumer, commercial or small business financing industry.
  • Prior software architecture and development experience in enterprise-grade platforms such as Ruby, Java, Go, or similar technologies, with a focus on building scalable, reliable, and high-performance systems.
  • Proven experience building enterprise systems on Salesforce and integrating it seamlessly into the overall enterprise architecture
  • Extensive experience with the Software Development Life Cycle (SDLC), leveraging Agile or other iterative frameworks to deliver high-quality software efficiently and effectively.
  • Prior experience in building robust, scalable platforms, particularly in fast-paced, dynamic environments.
  • Exceptional leadership skills that inspire and motivate teams, combined with an empathetic and thoughtful approach.
  • Proven ability to build strong, inclusive relationships across teams and stakeholders.
  • A passion for tackling complex technical challenges at scale and working closely with engineering teams to solve them.
  • Experience in facilitating and contributing to architectural design discussions to drive technical excellence.
  • A results-driven mindset, with a strong emphasis on leveraging data, achieving measurable outcomes, and maintaining high standards of software quality.

Good to Have:

  • FinTech industry experience, with a strong understanding of its unique challenges and opportunities.
  • Familiarity with small business lending, including workflows, underwriting processes, and customer needs.
  • Expertise in designing and implementing solutions that address regulatory and compliance requirements in financial services.
  • A track record of working in organizations that emphasize innovation, customer-centric problem-solving, and driving business value through technology.

#LI-MH1 #LI-Remote

Forward Financing Core Values:

  • Drive the Mission - We believe in financial opportunity for underserved small businesses. We say “yes” when others say “no.”
  • Keep It Real - We value direct communication, candid feedback, and authenticity. We are an open book.
  • Act With Kindness - We create an environment where caring is cool and helping is the norm. We do the right thing.
  • Shoot for Extraordinary - We are inspired by innovative thinking and continuous improvement. We never settle for yesterday’s best.

About Us:

Forward is a fintech company headquartered in Boston, Massachusetts with an affiliate office in Santiago, Dominican Republic, providing fast, flexible working capital to small businesses across the US. Forward offers revenue-based financing – delivering an upfront sum of working capital in exchange for a set amount of the business’s future revenue. By simplifying the requirements, streamlining the process, and using advanced proprietary technology, Forward is often able to deliver approvals within hours and funds that same day — giving more businesses the financial opportunity they need to thrive. Plus, with their dedicated teams and award-winning service, customers get personalized support when they need it most. 

Since 2012, Forward has expanded access to capital by providing over $3 billion in funding to nearly 63,000 small businesses. The company is A+ rated by the Better Business Bureau with an Excellent / 4.8 stars rating on Trustpilot.com. Forward is also recognized as a Best Place to Work by Built In Boston, certified as a Great Place to Work®, and is committed to helping their people and the small businesses they serve to achieve their full potential. 

Forward actively promotes a focus on diversity, equity, and inclusion in all we do. We encourage a workplace where trust and respect are paramount and all employees feel valued, heard, and accepted. Our diverse and driven group of about 450 people, with approximately 200 based in the US, and 250 in the Dominican Republic, is a 100% employee-owned company. Our people are excited about their work, knowing they are helping thousands of small businesses while advancing their own careers.

Perks & Benefits:

At Forward, our team members are at the heart of our company, and we are committed to taking care of them as people, not just employees. We offer a comprehensive benefits package, including but not limited to: medical, dental, vision, and commuter benefits, a flexible time-off policy, paid parental leave, 401k match for US employees, wellness reimbursement, volunteering days, annual professional development budget, and charitable donation match.

Workplace flexibility is a top priority at Forward too. Our Employee Choice policy means that almost all of our employees get to decide where they work. As a business, we are focused on impact; we are more concerned with your contributions to the success of the company than where you get your work done. If face-to-face time is desired, people managers are empowered to find a cadence that works for their team. 

When we aren’t collaborating to drive business and support our customers, we’re finding virtual and in-person ways to get to know our colleagues, celebrate team wins, and have fun together! 

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CEO of Forward Financing
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Average salary estimate

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What You Should Know About VP, Engineering, Forward Financing

At Forward Financing, we’re on the lookout for a visionary VP of Engineering to join our passionate team! This is an amazing opportunity for a software development enthusiast who’s eager to make a real impact in the fintech space. As a Boston-based company, Forward Financing is redefining how small businesses access working capital, and you will be a pivotal part of this mission. In this role, you will lead multiple engineering teams, collaborating closely with the Chief Technology Officer and various business unit leaders to deliver innovative, high-quality software solutions. You’ll inspire your teams, promote a culture of excellence, and focus on scaling our systems effectively while aligning with the organization’s goals. Your expertise in software architecture is crucial as you will guide architectural decisions and ensure that our platforms are robust and efficient. Moreover, we value diversity and are committed to creating an inclusive environment where everyone’s contributions are recognized and celebrated. The ideal candidate will have at least a decade of experience in software engineering leadership and a proven track record in building scalable systems—especially in the consumer financing sector. So if you’re ready to take on the challenge of empowering talented engineers and driving Forward Financing’s tech strategy, we want to hear from you!

Frequently Asked Questions (FAQs) for VP, Engineering Role at Forward Financing
What are the main responsibilities of the VP of Engineering at Forward Financing?

The VP of Engineering at Forward Financing is tasked with overseeing multiple engineering teams, ensuring alignment across various projects, and collaborating closely with the CTO and product management. This position requires demonstrating strong leadership, driving initiatives effectively, and fostering a results-driven engineering culture.

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What qualifications are required for the VP of Engineering position at Forward Financing?

Candidates applying for the VP of Engineering role at Forward Financing should have a minimum of 10 years of experience in software engineering leadership, including at least 5 years managing multiple teams. An extensive background in enterprise-grade platforms and familiarity with the fintech industry will be especially beneficial.

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How does Forward Financing define its engineering culture?

At Forward Financing, the engineering culture is centered around innovation, accountability, and customer-centric problem-solving. As VP of Engineering, you will play a vital role in championing this culture while empowering and inspiring your teams to achieve excellence in their work.

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What leadership qualities are sought after in a VP of Engineering at Forward Financing?

We look for exceptional leadership skills that inspire and motivate teams. The right candidate should embody an empathetic approach, fostering strong relationships across teams, and maintaining a results-driven mindset focused on leveraging data to achieve measurable outcomes.

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What should candidates be prepared for in an interview for the VP of Engineering position at Forward Financing?

Expect to discuss your leadership philosophy, your approach to software architecture, and how you've tackled complex technical challenges in the past. Forward Financing values candidates who can articulate their thought process and demonstrate their ability to foster collaboration and innovation.

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Common Interview Questions for VP, Engineering
How do you prioritize projects as a VP of Engineering?

Effective prioritization involves understanding both short-term and long-term business goals. Collaborate closely with product management and stakeholders to align on priorities based on impact and allow for flexibility when urgent matters arise.

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Can you describe your management style?

My management style is centered around empowering my team members while providing guidance when necessary. I believe in transparent communication and regularly soliciting feedback to foster a collaborative environment.

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What experience do you have with Agile methodologies?

I have extensive experience implementing Agile methodologies in various teams. I focus on iterative development, which allows teams to respond swiftly to changing requirements while delivering high-quality software efficiently.

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How do you ensure that your engineering team is continually improving?

By promoting a culture of learning, providing opportunities for professional development, and regularly reviewing performance metrics with the team. Feedback loops are essential in identifying areas of improvement and celebrating successes.

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What are some key metrics you use to measure engineering team performance?

I focus on metrics such as lead time, deployment frequency, and error rates. These metrics help assess team efficiency, quality, and the overall impact of engineering initiatives on business objectives.

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What is your approach to recruiting engineering talent?

My approach involves seeking out candidates who align with our values while possessing the required technical skills. I value diversity and inclusivity, ensuring our hiring process is equitable and accessible to all.

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How do you handle conflicts within your engineering teams?

I address conflicts directly and promptly by facilitating open discussions where all parties can voice their perspectives. It’s essential to foster trust, and a quick resolution will enable the team to focus on their goals.

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Can you provide an example of a technical challenge you solved?

In my previous role, we faced scalability issues as user demand surged. By implementing microservices architecture, we improved performance and allowed teams to work more autonomously, which significantly boosted our output.

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What strategies do you employ to align engineering initiatives with business goals?

I maintain regular communication with business leaders to understand their objectives. This ensures that our engineering projects are strategically tied to broader business priorities and can deliver the desired impact.

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How do you stay current with emerging technologies in the industry?

I dedicate time to ongoing education through webinars, conferences, and professional networks. Engaging with the tech community helps me stay informed about the latest trends and innovations that we may leverage in our engineering practices.

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Our mission is to build a world-class fintech company so that our customers and our people can achieve their full potential.

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BENEFITS & PERKS
Dental Insurance
Disability Insurance
Flexible Spending Account (FSA)
Vision Insurance
Performance Bonus
Family Medical Leave
Paid Holidays
FUNDING
DEPARTMENTS
SENIORITY LEVEL REQUIREMENT
TEAM SIZE
EMPLOYMENT TYPE
Full-time, remote
DATE POSTED
January 1, 2025

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