Best Firms To Work For
- Goran Gmitrovic
- Nov 12, 2025
- 8 min read
Updated: Jan 6
The 2025 Best Firms to Work For: Outlook Accounting & Taxes
# 1 - Boutique Firm Category
HEADQUARTERS: Chicago
NUMBER OF BILLABLE CONSULTANTS: 34

CLIENT INDUSTRIES SERVED: CPA Firms, Health Care, Consumer Services, Aviation & Aerospace, Construction, Entertainment, Financial Services, Farming, Food & Beverages, Information Technology Service, Real Estate , Marketing and Advertising, Media Production, Pharmaceutical
CONSULTING SERVICE LINES: Financial Consulting, Tax Advisory, Accounting Operations,
Outlook Accounting & Taxes is more than a traditional accounting firm, we are a strategic advisory partner dedicated to helping businesses and individuals achieve long-term success. Our work spans a wide range of services, including advisory, tax compliance and planning, financial planning, tax strategies, bookkeeping, payroll and CFO-level insights. By combining technical expertise with forward-thinking strategy, we provide clients with more than just accurate numbers, we deliver clarity, direction and confidence.
We specialize in simplifying the complex and unlocking opportunities for growth. Our team works closely with clients to design tax and financial strategies that go beyond compliance, creating roadmaps that maximize profitability, minimize risk, and position them for future success. From entrepreneurs building their first business to established organizations navigating expansion, we tailor solutions that align with their goals, values and vision.
Every service we deliver is rooted in excellence, precision and innovation. We believe that numbers alone don’t tell the full story, they need to be connected to strategy, leadership and execution. What sets Outlook apart is our relentless commitment to impact: we don’t just report results, we help shape them. We are partners in growth, trusted advisors and drivers of meaningful change.
CMAG: What characteristics and elements would you attribute to your firm’s inclusion as a Best Firm to Work For?
Our inclusion among the Best Firms to Work For is no accident—it’s the result of an intentional culture built around leadership, accountability and impact. At Outlook, we don’t take a back seat to our clients’ success, we drive it. Every service we deliver is led by leaders at the helm who are empowered to make decisions, challenge convention and create value. We don’t hire passengers for the journey; we hire drivers—individuals who bring fresh ideas, own their roles, and add meaningful contributions to every engagement.
We have built a firm where greatness is the standard, not the exception. Our professionals are expected to lead, grow and push boundaries, but they are supported every step of the way with mentorship, collaboration and the resources to succeed. Our culture thrives on a balance of high performance and genuine care, every team member knows they are part of something bigger, and that their impact matters.
What makes us stand out is not just what we do, but how we do it. We align every client engagement with leadership principles, ensuring that our people don’t just deliver a service, they deliver transformation. We cultivate a culture where accountability and empowerment meet, where innovation is not optional but required, and where collaboration fuels results.
Ultimately, our recognition as a Best Firm to Work For comes from building an environment where people are challenged to grow, inspired to contribute, and proud to be part of a firm that values both excellence and humanity.
CMAG: Are there any specific programs or initiatives that contributed to you being included as a Best Firm?
The programs and initiatives that have shaped our recognition as a Best Firm to Work For are centered on clarity, growth and empowerment. We set direct expectations with every team member so there is never ambiguity about what success looks like. We don't have role expectations, rather each team member has curated expectations and responsibilities that drive their growth and success. From day one, we pair expectations with the tools, training, and mentorship needed for each individual to thrive. Our goal is not to simply provide jobs, it is to build careers and leaders.
One of our most impactful initiatives is ensuring our professionals are placed on engagements that excite them. We believe that passion and performance go hand in hand. By aligning people with projects that match their interests and strengths, we fuel engagement, creativity and long-term retention. In addition, we intentionally assign “stretch roles” to push team members beyond their comfort zones. This philosophy, getting comfortable with the uncomfortable, has accelerated professional growth across our firm and given our people the confidence to lead at every stage.
Collaboration is also key. We cultivate an environment where ideas are shared openly, where competitiveness is healthy and fuels growth, and where people are celebrated for driving impact. Our programs blend structured learning with real-world responsibility, ensuring that our professionals are never stagnant.
These initiatives aren’t just check-the-box programs; they reflect our philosophy that the best investment we can make is in our people. That commitment is why Outlook is recognized as one of the Best Firms to Work For, and it’s why our culture will continue to thrive.
CMAG: In describing your firm, what would you say sets it apart from other consulting firms?
What sets Outlook apart is our refusal to be confined to the boundaries of a traditional consulting or accounting firm. While others may focus narrowly on tax compliance or basic advisory, we are actively building and expanding service lines that anticipate the future of business. We combine tax, advisory, financial planning, payroll and CFO-level services into an integrated solution that empowers clients with more than information, we provide strategy, foresight and execution.
Unlike firms that deliver only what is requested, we bring leadership to every engagement. We don’t sit in the background, we guide, challenge and drive outcomes. Our culture of accountability ensures that every client interaction is met with ownership, not passivity. This is why we only hire individuals who are drivers, not passengers, those who can elevate the conversation and add value and provide the confidence in clients. Our forward-looking mindset is what truly sets us apart. We are not only perfecting existing service lines, but we are also building new ones that expand the definition of what an accounting and advisory firm can be. From tech-enabled solutions to emerging advisory practices, our goal is to meet clients where they are while preparing them for what’s next.
Ultimately, what differentiates Outlook is the combination of depth and innovation. We pair the technical expertise of a traditional accounting firm with the entrepreneurial spirit of a modern advisory firm. This dual identity positions us not just as accountants or consultants, but as strategic partners who drive growth and change.
CMAG: Where your workforce is concerned, what would you say your priorities look like for the upcoming year and beyond?
Our workforce priorities reflect both the scale of our ambition and the depth of our commitment to our people. We are preparing for aggressive growth, with plans to double our workforce by the end of 2026. This expansion is fueled by the development of new national partnerships that will extend our reach, support our services, and provide exciting opportunities for our professionals to engage on larger platforms.
But our growth is not just about numbers, it’s about building the right leadership. We are consistently identifying and developing leaders who can drive the business forward, manage growth responsibly, and embody the culture of excellence we have created. Leadership development is central to our future priorities, ensuring that every layer of the firm has visionaries capable of inspiring teams and delivering results.
Another workforce priority is maintaining our unique culture as we scale. Growth brings complexity, but our focus is to preserve the entrepreneurial, collaborative, and empowering environment that earned us recognition as a Best Firm to Work For. That means continuing to invest in professional development, aligning roles with passions, and putting people in positions that challenge them to lead.
Ultimately, our workforce priorities are clear: expand with purpose, develop leaders, and build a culture that scales with growth. Our people are the foundation of our success, and our investment in them is the clearest path to achieving the bold future we envision.
CMAG: What opportunities do you see as the most promising?
The most promising opportunities lie at the intersection of technology, talent and transformation. New technologies, particularly automation and intelligent workflows, are revolutionizing the accounting and advisory industry. Rather than fearing automation, we see it as an enabler. By removing repetitive tasks, technology frees our professionals to focus on the higher-value work they desire: advisory, strategy and innovation. This shift not only improves efficiency but also accelerates learning and skill development, organically driving business growth.
We also see opportunity in the way clients’ needs are evolving. Businesses are looking for firms that can do more than balance books, they need partners who can guide them through complexity, help them grow and anticipate market shifts. Our integrated service model positions us uniquely to meet these demands by providing everything from tax planning to long-term financial strategy.
Finally, global expansion and partnerships represent another horizon of opportunity. By building new service lines and collaborating nationally and internationally, we are positioning ourselves as a firm that operates at scale but delivers with the agility of a boutique.
The most promising opportunity, however, is in our people. With the right talent, supported by the right technology, we can create limitless possibilities for growth, for our clients, our firm and our industry.
CMAG: What market forces do you see as the most challenging?
One of the most challenging market forces today is the rapid rise of artificial intelligence. While AI offers efficiency, it has become a crutch for many in our industry, leading to over-reliance and a loss of the human element that makes financial services meaningful.
Competencies are being diminished when professionals bypass critical thinking in favor of automated outputs. This creates risk, not only in quality of service but also in client trust.
At Outlook, we are intentional about how we leverage AI. We use it as a tool, not a replacement. We apply it ethically and responsibly, ensuring that technology enhances, rather than diminishes, human judgment. Our philosophy is clear: the future of this profession belongs to firms that can balance innovation with integrity, and technology with human expertise.
Beyond AI, another challenge is the pace of change itself. The accounting and advisory industry is facing shifting regulations, evolving client expectations and increasing competition. Firms that cannot adapt quickly risk being left behind. Our strategy is to embrace agility, continuously evolving our service lines, training our professionals to lead through uncertainty, and staying proactive in anticipating change.
The challenges are real, but they are also opportunities. By refusing to over-leverage technology and staying grounded in human intelligence, we will not only overcome these forces, we will set the standard for excellence in a changing market.
CMAG: What impact do you think Best Firm to Work For honors will have on your employees? The firm overall? Clients?
Being recognized as a Best Firm to Work For will have a profound impact on every aspect of our organization. For our employees, it is validation, proof that their hard work, leadership, and commitment to excellence are seen and celebrated. It fuels confidence, reinforces our mission, and inspires our people to continue growing with pride in their careers.
For our firm overall, this honor cements our place as an innovator and leader in the industry. It distinguishes us not just as another accounting firm, but as a respected organization shaping the future of our profession. It strengthens our ability to attract top talent, build new partnerships, and expand our influence nationally and internationally.
For our clients, this recognition is a powerful signal. It tells them that they are not working with a local or regional firm, but with one of the best in the industry, a firm that delivers excellence because it is built on excellence. It reaffirms our values, our credibility, and our ability to drive meaningful outcomes.
Ultimately, this honor is more than an award, it is a catalyst. It will propel us forward, inspire innovation, and confirm that our vision of building a firm that is both people-first and industry-leading is not only possible, but already being realized.
