Owner and Principal, Nichole Bailey, officially launched The Bailey Inc. after a career spanning more than a decade for Fortune 100 giants, American Express, Morgan Stanley and Chase. With a bachelor’s degree from Baruch College, leadership certificate from Harvard and over 15 years of industry experience, Nichole is a visionary, who has navigated operational strategies for major companies such as Viacom, Hilton, Delta, Groupon and Samsung.  

Her affinity for managing small businesses and catapulting them to success is her motivation.  With an affinity for understanding the importance of sustaining small businesses, The Bailey Inc.’s goal is to be a valuable asset in small business operations. Small businesses are the lifeline of the economy.  They are the backbone to the country’s jobs, innovations, and competitiveness.  

Nichole Bailey is known for her innate ability to translate a firm’s Needs, Problems and Goals into clear actionable business objectives. A strong global, cross-functional and transformative leader with a proven track record of cutting through ambiguity to create vision and drive alignment.  Nichole deploys strategies to maximise investment and catapult brands to position them for success. 

Can you talk to us a little bit about your background story?

For as long as I can remember I’ve been the go to person for execution. I’ve always been solution oriented, with a focus on how we can make things better.  I attribute this mindset to my years in Corporate America.  You learn that in order to succeed, business problems and obstacles are navigation points, reflection points not roadblocks.  I leverage this approach with my clients.  We can figure out anything, giving up is not an option.   

Through my years in corporate sitting at key stakeholder meetings, I had an epiphany.  I desired to bridge the gap in management between corporate clients and small businesses.  I recognised the only difference in sustainability is that small businesses don’t have the luxury of having huge advisory teams comprised of lawyers, marketers, accountants, strategists etc.  Large companies can establish themselves in the marketplace and reinvent themselves continuously without impacting their bottom line.  Small companies usually have one opportunity to get it right.  The Bailey Inc offers small business management to these firms, centralising their advisory team to champion them to success and  sustainability.  

I’ve been in this industry for 10+ years and the height of this global pandemic has energised my commitment even further to support small businesses. They are the lifeline of this economy. I’m here to keep them going. 

How are you working with product based companies to scale their operations, so they can focus on efficiency, innovating and driving revenue?

A creative at heart, I love birthing new projects.  Working with small businesses allows me to take their business goals on like my own.  I roll up my sleeves and get started peeling back the layers of the onion.  The product is shiny, but I want to ensure it’s sustainable.  My team evaluates those areas to ensure a company can scale their business.  Usually getting to market is top priority for companies, however their client engagement, marketing strategies, financial management and day to day operations need a bit of TLC.  We uncover the pain points and create strategy to optimise those blind spots.  We’re not building just for today; we want to ensure our companies are set up for longevity.  Usually the areas that go unattended due to prioritisation and capacity are the small fires burning that no one notices until the flames are uncontrollable.  We come in and assess everything.  

You previously worked at renowned companies such as Fortune 100, American Express, Morgan Stanley and Chase over the pan of two decades.  Can you talk us through why you chose this particular career path, and what value do you see in your work that keeps you going in this industry field?

Interestingly I chose American Express as I came across them in a Working Mothers magazine publication.  They were ranked #3 on the top companies for working mothers in the U.S. I had given birth to my daughter and while on maternity leave knew I needed a company that supported my value system of work quality and the importance of “showing up as your authentic self”.  I’m a mother and needed the flexibility to grow my career while parenting.  I loved the quality of work that impacted the consumer.  I was and still am motivated by the end user.  What do they get out of this experience?  You feel great working on a project but does the person consuming/receiving it feel the same way?  I started launching more product based campaigns throughout my career. I would read in financial publications how consumers felt about the rollout of their FICO launch, or new card features and had an immense sense of pride knowing that my execution impacted the consumer positively. 

I started working on Amex’s Shop Small business campaign and my affinity for small businesses and their critical role in the economy grew.  I knew my next path would lead me to work with small businesses directly and manage their operations.  It’s been the best decision I’ve made.  I’m confident this is my calling in life.  Every job has prepared me for this moment.  

What would you say is the most important characteristic that makes an outstanding leader?

Leaders set the agenda.  They define what winning looks like.  They’re fearless, empathetic, they understand the heart of the people.  Strategy is  paramount for them. 

What do you think has contributed most to your own success?

My tenacity and work ethic have contributed to my success.  I’m committed to thriving and bringing others along in the journey.  I’ve picked up the moniker ‘Grace Under Fire’ from clients.  This speaks to my ability to keep a level head and always lead from a place of encouragement.  When business owners trust you with their most prized position you have to treat it like it’s your own.  You have to encourage them to keep going, striving and optimising. Giving them recommendations doesn’t change the landscape.  Showing them how to execute paves the way for their success.  

What are your 3 most preferred tools/apps/platforms to synchronise your workload and remain efficient?

I love (I can’t stress this enough) Dubsado. Dubsado has increased my bottom line and my client engagement process.  Everything is in one place; I can automate a lot of my processes which helps me prioritise my workload. Once clients are set up in the portal, all documents, contracts, progress updates, invoices, schedulers, and communications are centralised. No one has to sort through a million emails to find the last email.  It’s perfect. I also love Asana for project and timeline management.  The left side of my brain is all analytical. I need to check off to-do boxes, it makes me feel accomplished at the end of every day.  Asana keeps my clients on track too.  They know what to expect next.  Also I can’t live without Canva, for my pitches and strategy decks.  It gives life to my creativity.  

What is one low point and high point that you have experienced in your career so far?

A low point in my career has been this year and dealing with the fallout from the pandemic.  To witness the firsthand impact on clients that once thrived and have used up all of their financial savings and still can’t keep the doors open or their employees on the payroll has been heart breaking.  I’ve had to lead emotional discussions with their staff and break it to them that they were being furloughed for a period of time.  To see the investment and years of service from these companies that were open for 10, 20 years is something that will stay with me forever.  As a result I’ve conducted audits for our clients to assess areas they can pivot.  

The highlight in my career is every launch to market that I get to celebrate with my clients.  It’s an exhilarating feeling to move from ideation to execution.  Every time it feels like a birth.  Our clients become family.  To participate in their win, makes it worth it.  

What do you think are the greatest challenges for women in leadership positions and what would you like to see changed?  

The greatest challenges for women in leadership positions is the glass ceiling.  Walking into a business meeting (or now virtually) and being one of few women in the room among your male counterparts creates its own unconscious biases.  Entering a room as the minority also compounds this.  I’m focused on staying true to myself while playing to my strengths to become the change I seek.  I’ve built my career on building relationships and creating allies.  When people begin to see you for who you are, what can you contribute and less about your gender and race, we progress forward as a society.  

Lastly, what can we expect to see from you in 2021?

In 2021 my mantra is exponential growth.  My goal is to expand into mid-size business management.  I will also focus on more leadership opportunities by speaking on forums, publications that celebrate the contributions of women in leadership.  I’m also looking to further enhance my podcast platform showcasing leaders, strategies and trends in business.  2020 taught the world so much about sustaining.  I’m going to master the reigns and focus on maintaining for myself and my clients.   




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