Project Leadership in the AI Era

October 30, 2025

For over 15 years, I’ve led teams in delivering complex technology projects. In that time, one mantra has consistently defined the role of a project manager: adapt. We adapt to scope creep, shifting stakeholder requirements, and unforeseen blockers. Adaptation is critical to managing a project, but we have reached an inflection point where merely adapting is no longer enough. To simply react to the daily challenges of a project is to risk hitting deadlines and budgets, while failing to deliver real, sustainable value.

Redefining Project Leadership: Augmenting Your Strategy with AI

The rise of AI often sparks a conversation about what technology can do. I think the more important question is what it enables us to do. Technology is brilliant at handling the predictable, repeatable, and analytical parts of our work – forecasting risks, optimizing resource plans, and analyzing performance data. But it lacks the uniquely human qualities that define true leadership: empathy, strategic vision, creative problem-solving, and the ability to inspire a team.

The real transformation happens when we combine human insight with technological power. AI can process the data, but it takes a human to interpret the nuance. It can automate a workflow, but it takes a leader to foster a culture where that automation creates more value, not just more free time. Our goal shouldn’t be to compete with machines, but to leverage what inherently makes us human more than ever before.

Beyond Automation: The Pillars of Proactive Project Leadership

So, how do we make this shift from reacting to leading within the context of our projects? It comes down to a few key principles:

• Cultivate Relentless Curiosity: Proactive leadership begins with asking powerful questions that go beyond the project charter. Instead of just learning how to use a new tool, a proactive leader asks “Why?” until they uncover the true underlying need. This moves the conversation from “We need a new dashboard” to “Our users can’t find the data they need to make a decision.”
  
• Develop Strategic Foresight: Adapting is about dealing with the immediate impact of change. Leading is about anticipating the second and third-order consequences. This means asking, “And then what?” For example, a decision to add a “quick fix” to meet a deadline (a first-order-consequence) might seem smart. But a leader with foresight sees the second-order-consequence: that fix will create technical debt, slowing down the next three projects.
• Become a Creator or Builder: It can be easy to get trapped in an efficiency loop – just doing the same things, but faster. Proactive leadership challenges us to break that cycle. With AI handling optimization, we are freed up to build. This shifts our focus from simply delivering outputs (the “what”) to becoming creators of entirely new outcomes (the “why”). The question is no longer just, “How can we finish faster?” It’s, “How can we leverage this technology to build something more valuable, more innovative, and more impactful than what was originally planned?”
• Champion a Culture of Innovation: A leader’s most important role on a project is to create an environment where the team feels safe to take risks. We must empower our teams to experiment, to learn from failure, and to challenge the status quo. When a team member flags a mistake, a proactive leader’s response might be, “Thank you for catching that. What can we learn from this?” This approach transforms mistakes from liabilities into assets for learning and improvement.
  

Now Is The Moment

This isn’t a theoretical exercise for some distant future. The opportunity in front of every project leader right now is immense. The future isn’t something that just happens to us; it’s something we build, decision by decision. We can choose to manage the projects of tomorrow, or we can lead the vision for the day after.

The choice is ours. Let’s choose to lead.

Product Education: Building Trust, Informing Policy

May 29, 2025

In today’s fast-paced fintech landscape, the lines between departments are blurring – and for good reason. Our extensive experience in Marketing and Compliance has shown us the incredible power of genuine cross-functional collaboration, particularly when communicating about our product to diverse audiences, like customers, partners, vendors, and legislators. It’s no longer sufficient to simply market a product or ensure its compliance; we must actively educate. This approach is a strategic imperative that empowers our customers and drives fair, effective policymaking that benefits all.

Building Trust and Adoption

Fintech customers demand more than just a financing product; they need solutions that deliver transparency and clarity. Understanding how a product functions and its direct benefits is essential for them. We take ownership of proactively providing this insight. Effective product education is key here – by sharing straightforward educational content about our financial offerings, we build customer confidence, minimize friction, and foster strong loyalty.

A detailed funding call that breaks down terms, comprehensive self-serve resources, and readily available contact information all contribute to a customer feeling informed, secure, and supported. Our onboarding materials aren’t just instructions; they’re foundational guides. When customers understand our product, we see improved engagement, better performance, higher retention, and greater overall satisfaction. Simply put: more educated customers tend to be more successful business owners and ultimately more loyal customers – and that’s a win, win.

Driving Effective Policy

From a legal and policy standpoint, the value of simple, jargon-free, factual materials is tremendous. Legislators need a clear, accurate understanding of our product to create regulation that is both fair and effective. Policymakers often attempt to classify products into existing categories, so it’s critical that we articulate the nuanced differences between similar yet distinct offerings.

Consider the innovation in fintech over the past decade alone, particularly products like ours that allow businesses to pay according to their revenues. This concept often excites and impresses policymakers, because the benefits are immediately clear. However, the tendency of attempting to apply laws passed decades ago to these modern financial products often is like putting a square peg in a round hole. Those foundational laws were simply not designed for the kind of flexible, responsive financial solutions that exist today. Clear, proactive education helps bridge this gap, ensuring that new legislation is well-informed and doesn’t inadvertently stifle beneficial innovation for the many underserved by traditional financing institutions. By clarifying these distinctions, we contribute to a regulatory environment that supports progress.

Final Thoughts

Whether we’re earning customer loyalty or helping to inform legislation, education is fundamental to building long-term trust and fostering sustainable growth. To achieve this, we need to:

• Make education an ongoing strategic priority: This isn’t a one-off campaign; it’s a continuous commitment that evolves with changing customer needs and industry regulation.
• Align compliance with creativity: Our internal teams must collaborate closely, ensuring that marketing communications are easy to understand while also being fully compliant.
• Stay close in a fast-evolving industry: The fintech landscape is constantly changing. Marketing and Legal teams should partner early and often, both internally and externally, to ensure educational efforts remain relevant and impactful.

Safeguarding Ethical Alternative Financing

January 31, 2025

Access to capital remains a significant challenge for small businesses in the US, with nearly 50% of small business loan applications being declined, according to a 2024 Small Business Administration (SBA) report. Alternative financing has stepped in to fill this gap, but with that opportunity comes an important responsibility to operate with integrity, transparency, and fairness. Every company in the small business financing sector has a duty to each other to uphold ethical standards to support a healthy, thriving ecosystem.

At Forward, we believe that compliance is more than just following the rules, it’s about doing the right thing. By maintaining rigorous compliance standards, we’ve helped to build confidence in our services and foster long-term relationships with our customers and business partners. Here, we’ll explore three key methods to promote ethical standards in alternative financing.

• Provide Transparent Information – Small business owners should have a clear understanding of the funding they receive—what it costs, how payment works, and what terms apply. Confusing or vague disclosures can place unnecessary financial strain on customers. Funding providers should present information in a straightforward, easy-to-understand manner. Forward customers will always find the cost of our financing clearly outlined on the front page of our contract. By proactively adopting ethical practices like this, we protect both our customers and our business, while contributing to the overall integrity of the industry.
• Stay Ahead of Regulatory Changes – The regulatory landscape for small business financing is constantly evolving. In recent years, multiple states have introduced laws requiring commercial financing providers to disclose standardized terms to customers. These measures aim to help business owners compare financing options more effectively. Staying on top of these regulatory changes is crucial for compliance. Forward has a dedicated team monitoring new laws at both the state and federal levels, ensuring that company policies align with the latest legal requirements. Quickly and fully adapting to regulatory changes demonstrates our commitment to responsible financing.
• Cultivate a Culture of Ethical Business Practices – Beyond compliance with laws, companies should foster a culture of ethical decision-making. This means prioritizing the customer experience and ensuring fair treatment. When financing providers operate with integrity, they build trust with customers and support a more sustainable marketplace. Doing the right thing is embedded in our culture and core values at Forward, guiding the decisions we make every day—from our frontline team members to our executive team.

Final Thoughts

The need for alternative financing solutions for small businesses is clear. Yet, without proactively adopting responsible practices, the industry risks increased regulation that could further restrict the already limited funding options available. By prioritizing compliance, transparency, and ethical decision-making, we can collectively help to ensure that alternative financing remains a viable option for small businesses.

Reflections on Leadership, Growth, and Building for the Future

December 13, 2024

It’s an exciting time at Forward! As we prepare to welcome our new CEO, Jason Mullins, in the new year and our current CEO, Justin Bakes, transitions to the role of Executive Chairman, I can’t help but reflect on our incredible journey. Over the past 7 years at Forward, I’ve had the privilege of witnessing firsthand the leadership and dedication behind building not just a successful company, but a thriving team driven by a shared purpose. Providing hard-working small businesses, which are the backbone of our economy, with access to the working capital they need to succeed. We wanted to create a solution and build a mission-driven organization where talented people would be excited to run to work every day. That desire became the foundation of Forward.

The Foundation of Leadership

Looking back, I believe a few key principles have been essential to our success:

• Vision and Purpose – From day one, we’ve had a clear vision: to make working capital more accessible and empower small businesses. This purpose has fueled our passion and provided a guiding star for every decision we made.
• Transparent Communication – Open and honest communication is the foundation of our relationships with our team and our customers. We’ve worked hard to foster a culture where everyone feels comfortable sharing ideas and concerns, which is vital for collaboration and dynamic problem-solving.
• Adaptability – The business world is constantly evolving, especially in the fintech industry. Our ability to adapt to new challenges, embrace change, and maintain a solutions-oriented mindset has allowed us to navigate uncertainty and emerge stronger.

Lessons Learned in Leadership

The years I’ve spent at Forward have been a masterclass in leadership. I’ve gained invaluable insights that have shaped my own leadership journey and the way I approach challenges.

• Invest in People – Our people are truly our greatest asset. We have prioritized investing in their development, providing opportunities for growth, and cultivating an environment of continuous learning. This has expanded our collective expertise and created an engaged and loyal workforce.
• Culture and Values – Defining and nurturing our company culture has been crucial. Our values based on authenticity, transparency, innovative thinking, and customer focus – have shaped our identity and guided our interactions at every touchpoint.
• Strategic Planning – Sustainable growth requires careful planning. As we evolved, we developed clear strategies, set measurable goals, and put action plans in place to achieve them – with solid communication and progress tracking all along the way. This disciplined, proactive approach has helped us stay focused and make more informed decisions with greater collaboration and alignment across the organization.

Why a Deep Leadership Bench Matters

Building a strong, diverse leadership team is essential for achieving both immediate wins and building a sustainable future.

• Driving Innovation – Leaders at all levels have expanded our collective expertise, bringing diverse perspectives and ideas to the table. This fuels innovation and allows us to explore new possibilities.
• Ensuring Continuity – A deep leadership bench helps ensure that the company can seamlessly navigate transitions, whether planned or unexpected. This creates stability and confidence, both internally and externally.
• Supporting Growth – Strong leadership is essential for scalability and building effective, resilient teams. These leaders inspire and support their people, creating a culture where individuals are empowered to grow and develop professionally, which also contributes to the organization’s overall success.

Final Thoughts

As we embrace this next chapter, I’m confident in our ability to thrive through strong leadership, collaboration, and empowering our people to succeed. By fostering a culture that values resilience and teamwork, we’re well-positioned for continued success. With deep gratitude for our exceptional team, loyal customers, and trusted partners, I’m excited to see what we can continue to achieve together.

Enterprise Partnerships, Expansion Opportunities, and the Future of Fintech

November 18, 2024

As a venture capital investor for startups, company founder, and a former VP & GM at Upstart (NASDAQ: UPST), an online lending platform, I’ve seen how vital enterprise partnerships can be in shaping the future of a business. Fintech is evolving rapidly, and enterprise partnerships offer a key advantage—not just in driving innovation, but in unlocking new expansion opportunities. By effectively collaborating with the right partners, we can access new markets, integrate cutting-edge technologies, and enhance regulatory compliance in a way that wouldn’t be possible alone.

Importance of Enterprise Partnerships in Fintech

As the fintech landscape grows more interconnected and the financing gap for many US small businesses widens, strategic partnerships are becoming essential for driving accelerated innovation. These collaborations are key to expanding access to capital, supporting sustainable growth, and unlocking the limitless opportunities ahead. For us, it’s not just about competing today, but laying the groundwork for tomorrow.

What Makes for a Successful Enterprise Partnership?

• Aligned Vision & Goals: A successful partnership begins with a shared vision and mutually beneficial goals. Both parties must be honest and transparent, as misaligned objectives lead to wasted time and missed opportunities.
• Complementary Strengths: Each partner should bring a unique strength to the table, such as technology, market reach, data insights, or regulatory expertise.
• Customer-Centric Focus: Partnerships should prioritize creating value for customers, addressing pain points, and enhancing the user experience.
• Open & Transparent Communication: Establishing clear lines of communication is essential to promptly addressing challenges and leveraging opportunities.
• Scalability & Flexibility: The ability to scale the partnership and adapt to changing market dynamics is a crucial consideration for success.
• Long-Term Commitment: Building trust through a long-term approach, where both parties are committed to sustained growth and evolution.

What Are Some Best Practices for Working with Enterprise Partners?

• Establish Clear Roles & Responsibilities: Define the roles, responsibilities, and expectations for each partner upfront to ensure seamless collaboration.
• Set Joint KPIs: Develop a framework for measuring success, including shared Key Performance Indicators (KPIs) and metrics to track progress.
• Invest in Regular Check-Ins: Consistent communication, feedback loops, and regular check-ins to ensure alignment and address any issues.
• Leverage Technology for Integration: Use technology to facilitate smooth data sharing, streamline processes, and enable efficient integration of systems.
• Risk Management & Compliance: Work together to identify and mitigate risks, ensure compliance, and keep pace with regulatory changes.
• Celebrate Wins & Learn from Failures: Recognize achievements and review any setbacks to continuously improve the partnership.

Where Fintech Is Going?

It’s truly incredible how fast the fintech industry is evolving. What was once a niche market has grown into a dynamic and innovative space that’s reshaping how we think about finance. Whether it’s through digital payments, AI-driven funding, or personalized financing experiences, the possibilities seem endless.

• Focus on Financial Inclusion: Fintech companies are driving financial inclusion, providing access to financing for underserved segments of the market.
• Personalization via AI & Data Analytics: AI and data analytics are playing a pivotal role in underwriting, risk assessment, and personalizing financing offers to better match the specific funding needs of businesses.
• Increasing Demand for Alternative Financing: The growing demand from small- and medium-sized businesses for flexible financing options has increased, especially as traditional lending criteria have tightened.
• Expanding Potential for Embedding Finance: There is a growing opportunity to embed finance, where alternative financial products are integrated into non-financial platforms to reach users in a convenient manner for them.
• API-Driven Models: API frameworks are fostering interoperability, enhancing product offerings, and making partnerships more seamless.

Final Thoughts

As we look toward the future, it’s clear that fintech will continue to break boundaries and redefine how small businesses access working capital. Working with strategically aligned partners allows us to create powerful ecosystems that deliver more value to customers and drive growth for all involved. Ultimately, it’s about finding partners who share your vision and complement your strengths.