Upskilling and Reskilling: How to Close the Talent Gap on Your Way Up the Corporate Ladder

Upskilling and Reskilling: How to Close the Talent Gap on Your Way Up the Corporate Ladder

Upskilling and reskilling are terms you probably hear often. Perhaps you aren’t fully aware of the nuances or why they’re so essential for career success.

In today’s workforce, skill gaps abound. Over 80% of talent development professionals note a skill gap in their organization, with 78% anticipating them down the line. If you can make upskilling and reskilling a priority, you’ll be well on your way to corporate success in today’s agile workforce.

Here’s everything you need to know about upskilling and reskilling.

Upskilling and Reskilling Meaning: The Differences

When it comes to upskilling yourself or even reskilling, it’s essential to understand the differences between the two. While both involve closing your skill gap and becoming a more effective employee, they’re fundamentally different.

Upskilling refers to improving upon your existing skills and strengthening your current understanding. Upskilling examples include becoming a better communicator to take on a managerial position or learning how to forecast your company’s financials more accurately when preparing to be CFO.

In general, upskilling refers to staying within your vertical and expanding your current skills.

Reskilling is the opposite of upskilling in that it involves learning an entirely new set of skills. Doing so should prepare you to take on a different or more broad role. Select-few circumstances can create the need to reskill. These include advances in technology that make current responsibilities less relevant or the decision to make a career pivot where entirely new skills are required.

As opposed to upskilling, reskilling refers to stepping out of your current vertical and expanding your total knowledge.

How Upskilling and Reskilling Impact Your Career Path

If you’re setting your sights on climbing the corporate ladder, both upskilling and reskilling will benefit you. In senior positions, you’ll be asked to take on a wide variety of tasks (reskilling required) and be highly knowledgeable about your primary verticals (upskilling required).

No matter where you are in your career, focus on the following:

  • Look for companies that prioritize employee development (more on this in a later section). Your employer should create a culture of talent mobility where employees are motivated and encouraged to take on upskilling and reskilling.
  • Identify your hidden skills. It takes concentrated effort to be in touch with your strengths (and weaknesses). For instance, if you know you’re a good communicator, your other “hidden skills” may include teaching, leading, and influencing (i.e. if you’re good at communicating, you’re also probably good at teaching others). Being in touch with these hidden skills allows you to apply them, making you a more valuable employee and progressing your career – more on how to identify these hidden skills here.
  • Meet future demand. Depending on where you are on your career journey, upskilling and reskilling can help you meet future needs. If your sights are set on a senior position, the nature of your responsibilities will change. Being prepared for the demands of those future positions means you can upskill and reskill to help you succeed down the line.

Everyone Should be Upskilling and Reskilling. Here’s How: 

No matter where you are on the corporate ladder, if your sights are set on climbing it, you need to prioritize upskilling and reskilling from now. Here’s what you can do to make sure that doesn’t fall by the wayside.

Option 1: Find Employers Who Prioritize Employee Development

There’s a stark contrast between employers who care deeply about your career progression and those who don’t. Employee development should be part of your current employer’s ethos;  upskilling employees (and reskilling) are significant parts of this.

Some examples of employee development include:

  • Conferences that allow you to develop specific hard or soft skills
  • Regular one-on-ones where managers can provide honest feedback
  • Peer mentorship programs so you can learn from the experiences of others
  • Educational stipends allow you to enhance your skills through learning experiences (more schooling, subscriptions to industry publications, etc.)
  • A culture that encourages upward mobility – all of the above can contribute to this

Option 2: Find a Mentor

If your company doesn’t offer peer mentorship programs, it’s time to tap into your network to find a mentor. Look for people whose career paths and successes you’d like to emulate. For instance, if you’re looking to be CEO one day, find a CEO you admire.

This mentor can help you identify what upskilling and reskilling you need to do.

Not sure how where to find these mentors? If you don’t know anyone directly, ask around. You can also try searching for people on LinkedIn, but make sure you take the time to get to know someone first before making the big ask. Mentorship is a huge favor and not to be taken lightly.

Option 3: Get More Education

Further education can be an excellent option when it comes to upskilling and reskilling. Even if your company doesn’t offer educational stipends (though you should check), consider getting an MBA or some other form of higher education. These programs can help you upskill and reskill to prepare for a senior position.

Option 4: Know Your Worth

By now, you should understand the importance of upskilling and reskilling. 

Ultimately, the demand for a well-trained workforce is high, with companies such as PwC and Amazon placing a heavy focus on it – and investing hundreds of millions (or billions). Companies are waiting to help you break into that senior position you want. If you’re unsatisfied with your current company and feel you could grow better elsewhere, it’s time to move on.

Jennings Executive has over two decades of combined experience matching qualified candidates with outstanding companies. If you’re looking to upskill or reskill into a more senior position, we can help. And if you aren’t quite ready for that yet, we’d still love to get to know you! Learn more today. 

Final Word

Upskilling and reskilling throughout your career are essential to climbing the corporate ladder. Reskilling refers to learning new skills outside your current expertise, whereas upskilling refers to strengthening your current ones.

We hope this article helped you clarify upskilling vs. reskilling and the importance of both!

Kerry Ward

Director of Strategic Operations

Kerry is the Director of Strategic Operations at Jennings Executive Search. Starting her career with a boutique bank management consulting firm specializing in revenue enhancement and regulatory compliance, her engagements with financial institutions within all 12 Federal Reserve Districts propelled her interest for blending client interaction and strategic financial operations. She later transitioned to tax consulting and wealth management becoming registered with FINRA and the SEC and becoming licensed in insurance. Moving into a big four investment bank, and working in a boutique ultra high net worth investment advisory firm, her history spans various aspects of capital markets – both public and private.


Here at Jennings Executive Search, Kerry applies her two decades of experience along with her knack for interpersonal communications in aligning the interest of all stakeholders. Joining the team was a natural return to a highly specialized firm where she can work across all business functions using her energetic candor, enthusiasm for growth and improving processes while fostering relationships with our clients to reach their talent development and overall strategic growth goals.


Kerry graduated with a Bachelor of Business Administration degree from Georgia State University, and earned her MBA in Finance. Outside of the Jennings office, she enjoys traveling with her family for outdoor music festivals, golf and sports.

Daniel Wilkinson

Vice President of Strategic Initiatives & Client Success

DANIEL WILKINSON IS THE VICE PRESIDENT OF STRATEGIC INITIATIVES & CLIENT SUCCESS. HE BRINGS OVER TWO DECADES OF EXPERIENCE IN COMMERCIAL AND PRICING STRATEGY, HAVING HELD KEY LEADERSHIP ROLES AT DELTA AIR LINES AND DELTA VACATIONS. HIS CAREER IS MARKED BY A PROVEN TRACK RECORD IN DRIVING SIGNIFICANT BUSINESS TRANSFORMATION THROUGH INNOVATIVE DATA-DRIVEN STRATEGIES, CROSS-FUNCTIONAL TEAM LEADERSHIP, AND ENHANCED PROFITABILITY. DAN’S EXPERTISE IS IN HIS ABILITY TO INTEGRATE DATA ANALYTICS WITH STRATEGIC PLANNING, ENABLING ORGANIZATIONS TO OPTIMIZE THEIR REVENUE MANAGEMENT AND PRICING STRATEGIES IN DYNAMIC MARKET ENVIRONMENTS.

AT DELTA VACATIONS, DAN SERVED AS VICE PRESIDENT OF STRATEGIC BUSINESS/IT PLANNING & REVENUE MANAGEMENT, WHERE HE SUCCESSFULLY LED TEAMS IN DELIVERING SCALABLE TECHNOLOGY SOLUTIONS, DEFINING GO-TO-MARKET STRATEGIES AND DRIVING SIGNIFICANT INCREMENTAL REVENUE AND PROFIT.

DAN RECEIVED A BACHELOR OF SCIENCE FROM TAYLOR UNIVERSITY AND AN MBA WITH A FINANCE CONCENTRATION FROM EMORY UNIVERSITY’S GOIZUETA BUSINESS SCHOOL.

Brian Banister

EXECUTIVE RECRUITER

BRIAN BANISTER IS AN EXECUTIVE RECRUITER AT JENNINGS EXECUTIVE SEARCH. BRIAN HAS A BROAD RANGE OF EXPERIENCE, HAVING WORKED IN STRATEGY & CORPORATE DEVELOPMENT, FINANCIAL PLANNING & ANALYSIS, AND PUBLIC ACCOUNTING ROLES FOR LEADING COMPANIES AND CLIENTS IN THE HOSPITALITY, REAL ESTATE, MANAGEMENT CONSULTING, AND TECHNOLOGY, MEDIA, AND TELECOM (TMT) SECTORS. HE BEGAN HIS CAREER AT DELOITTE & TOUCHE, WORKING AS A LICENSED CPA. AFTER DELOITTE, BRIAN PIVOTED INTO CORPORATE FINANCE, WHERE HE HELD POSITIONS IN STRATEGY & CORPORATE DEVELOPMENT AT INTERCONTINENTAL HOTELS GROUP (IHG) AND COX COMMUNICATIONS, AS WELL AS AN FP&A ROLE AT BOSTON CONSULTING GROUP (BCG). THESE ROLES ALLOWED BRIAN TO GAIN VALUABLE EXPOSURE IN AREAS LIKE CLIENT SERVICES, STRATEGIC CONSULTING & PLANNING, FINANCIAL ANALYSIS, AND M&A AND INVESTMENT ACTIVITY.

BRIAN’S EDUCATION INCLUDES BOTH A MASTER OF ACCOUNTANCY DEGREE AND A BACHELOR OF BUSINESS ADMINISTRATION IN ACCOUNTING FROM THE UNIVERSITY OF GEORGIA.

Lori Shad

EXECUTIVE RECRUITER

DRIVING TRANSFORMATION THROUGH PEOPLE IS OUR MISSION AND LORI’S PASSION AS AN EXECUTIVE RECRUITER WITH JENNINGS EXECUTIVE SEARCH. SHE CONDUCTS THOROUGH RESEARCH ON EACH ROLE AND BUILDS STRONG RELATIONSHIPS WITH CANDIDATES TO HELP CONNECT PROFESSIONALS WITH THEIR NEXT GREAT OPPORTUNITY. LORI SPENT 22 YEARS AT A FORTUNE 500 INSURANCE COMPANY IN PRODUCT MANAGEMENT, SALES/BUSINESS CONSULTING, AND RECRUITING ROLES. SHE USES THIS EXPERIENCE AS SHE SEARCHES FOR THE BEST TALENT TO HELP DRIVE CLIENT SUCCESS FORWARD. SHE’S FOCUSED ON DELIVERING RESULTS AND GETS THERE THROUGH EFFICIENCY AND TENACITY WITH AN EMPATHETIC, COMPASSIONATE, FUN, GENUINE, AND POSITIVE APPROACH. SHE HAS BEEN INSTRUMENTAL IN HELPING CLIENTS ACHIEVE BUSINESS OBJECTIVES THROUGH UNDERSTANDING NEEDS, CREATING INDIVIDUAL, DATA-DRIVEN SOLUTIONS, AND SOLVING PROBLEMS, AS WELL AS POSITIVE RELATIONSHIP BUILDING AND TEAMWORK.

LORI GRADUATED WITH A BACHELOR OF SCIENCE DEGREE FROM THE UNIVERSITY OF GEORGIA.

Justin Graves

EXECUTIVE RECRUITER

JUSTIN GRAVES IS AN EXECUTIVE RECRUITER AT JENNINGS EXECUTIVE SEARCH.

JUSTIN HAS A VARIETY OF EXPERIENCES WORKING WITHIN PUBLIC AND INDUSTRY ACCOUNTING. HE BEGAN HIS CAREER WITH PATHSTONE FAMILY OFFICE PREPARING TAX RETURNS FOR HIGH NET WORTH INDIVIDUALS AND CORPORATIONS IN THE ATLANTA AREA. IN JANUARY 2015, HE JOINED COHNREZNICK, LLP, A TOP 10 PUBLIC ACCOUNTING FIRM, IN AUDIT & ASSURANCE WORKING PRIMARILY IN THE COMMERCIAL REAL ESTATE AND HOUSING MARKET. PRIOR TO JOINING JENNINGS EXECUTIVE SEARCH, JUSTIN WORKED AT A FAST GROWING TECHNOLOGY COMPANY, SS&C TECHNOLOGIES, WHERE HE WORKED IN THE REAL ASSETS DEPARTMENT DOING FUND ADMINISTRATION.

JUSTIN GRADUATED WITH A BACHELORS OF SCIENCE DEGREE IN ACCOUNTANCY FROM OGLETHORPE UNIVERSITY.

Justin Jennings

EXECUTIVE RECRUITER

JUSTIN JENNINGS IS AN EXECUTIVE RECRUITER AT JENNINGS EXECUTIVE SEARCH. HE COMES FROM THE HEALTHCARE INDUSTRY WITH 15 YEARS OF MEDICAL SALES EXPERIENCE. HE ATTRIBUTES HIS SUCCESS IN SALES TO LISTENING AND LEARNING FROM HIS CUSTOMERS AND ENJOYS THE PROCESS OF SOLVING PROBLEMS. HE IS SKILLED AT DEVELOPING THE RIGHT ACTION PLAN FOR EACH OF HIS CLIENT’S UNIQUE NEEDS AND COMMITTED TO HELPING THEM CHOOSE THE BEST SOLUTION. JUSTIN HAS TAKEN HIS SPIRIT AND PASSION FOR SELLING TO THE WORLD OF RECRUITING. HE HAS A GOAL OF SURPASSING HIS CLIENT’S EXPECTATIONS AND ASSISTING THEM WITH TALENT ACQUISITION.

JUSTIN GRADUATED WITH A BACHELOR OF SCIENCE IN MANAGEMENT FROM GEORGIA INSTITUTE OF TECHNOLOGY. WHEN NOT AT WORK, YOU CAN FIND HIM ON HIS MOUNTAIN BIKE, THE GOLF COURSE, OR SKIING OUT WEST IN THE WINTERS.

Chip Locke

PRACTICE LEAD, TECHNOLOGY RECRUITING

CHIP LOCKE IS THE TECHNOLOGY RECRUITING PRACTICE LEAD FOR JENNINGS EXECUTIVE SEARCH. CHIP BRINGS 15 YEARS OF EXPERIENCE IN TECHNOLOGY AND RECRUITING INCLUDING HANDS-ON WORK AS A SOFTWARE DEVELOPER AND BIG 4 SYSTEMS CONSULTANT. HE IS A TRUSTED CIO ADVISOR WITH EXPERIENCE ACROSS INDUSTRY VERTICALS AND A DEEP UNDERSTANDING OF TECHNOLOGY PLATFORMS AND THE FUNCTIONAL AREAS OF DELIVERY THAT ENABLE BUSINESS OPERATIONS. HIS EXPERIENCE INCLUDES RECRUITING EXECUTIVES AND COLLABORATING ON STRATEGIC PLANNING AND IMPLEMENTATION OF IT ORGANIZATIONS.

HIS CLIENT SUCCESS STORIES CAN BE FOUND AT COMPANIES RANGING IN SIZE FROM STARTUP TO FORTUNE 500 ACROSS AVIATION, ENERGY, FINANCE, HEALTHCARE, TECH, MANUFACTURING, RETAIL AND TELECOMMUNICATIONS. CHIP GRADUATED FROM THE UNIVERSITY OF GEORGIA WITH A BACHELOR OF BUSINESS ADMINISTRATION DEGREE IN MANAGEMENT INFORMATION SYSTEMS.

Brian Gelfand

PARTNER

BRIAN GELFAND IS A PARTNER AT JENNINGS EXECUTIVE SEARCH. HE BEGAN HIS CAREER AT DELOITTE & TOUCHE IN AUDIT AND ENTERPRISE RISK SERVICES, WITH A FOCUS ON THE FINANCIAL SERVICES AND REAL ESTATE INDUSTRIES. AT DELOITTE, BRIAN GAINED VALUABLE CORPORATE EXPERIENCE WORKING WITH A MULTI-BILLION DOLLAR PUBLIC MORTGAGE SERVICING CORPORATION, AND A NOT-FOR-PROFIT FOUNDATION WITH OVER $10 BILLION IN ASSETS. BRIAN PASSED THE CPA EXAM BUT ULTIMATELY DECIDED ASSISTING CLIENTS WITH THEIR PEOPLE STRATEGIES WAS HIS PASSION.

BRIAN’S EDUCATION INCLUDES A MASTER OF ACCOUNTANCY FROM KENNESAW STATE UNIVERSITY AND A BACHELOR OF BUSINESS ADMINISTRATION IN ACCOUNTING FROM GEORGIA COLLEGE & STATE UNIVERSITY

Jon Jennings

FOUNDER / MANAGING PARTNER

JON JENNINGS IS THE FOUNDER AND MANAGING PARTNER OF JENNINGS EXECUTIVE SEARCH. ESTABLISHED IN 2014, HIS VISION WAS TO SHAPE A FIRM ANCHORED IN TRANSPARENCY AND VALUE CREATION. OVER THE YEARS, JON HAS HAD THE DISTINCT OPPORTUNITY TO ENGAGE WITH AND LEARN FROM LEADING INDUSTRY EXECUTIVES, GLEANING INSIGHTS FROM THEIR EXPERIENCES AND COMBINING THIS KNOWLEDGE WITH THOROUGH RESEARCH. THIS HAS EQUIPPED HIM TO OFFER A DEEPER, MORE STRATEGIC PERSPECTIVE ON ORGANIZATIONAL DESIGN AND TALENT IDENTIFICATION. WITH AN INITIAL FOCUS IN FINANCE, THROUGH JON’S LEADERSHIP THE FIRM HAS PIVOTED INTO BROADER COMMERCIAL AND TECHNICAL STRATEGIES AS WELL AS PROFESSIONAL SERVICES.

TOGETHER WITH HIS EXPERIENCED TEAM OF EX-CONSULTANTS AND INDUSTRY PROFESSIONALS, JON COLLABORATES WITH PREMIER CONSULTING FIRMS TO ENHANCE THEIR PRACTICES. SIMULTANEOUSLY, HE ASSISTS PRIVATE EQUITY GROUPS AND THEIR PORTFOLIO COMPANIES IN REFINING AND FORTIFYING THEIR COMMERCIAL AND FINANCIAL STRATEGIC OPERATIONS.

THE CULMINATION OF THESE EFFORTS IS A BOUTIQUE FIRM THAT INC.COM CELEBRATED AS ONE OF THE COUNTRY’S FASTEST-GROWING COMPANIES. BETWEEN 2019 AND 2022, THE COMPANY WITNESSED A STAGGERING GROWTH RATE OF NEARLY 600%.