Career Progress 101 for Senior Positions: 8 Tips For Breaking Into That Senior Role

Career Progress 101 for Senior Positions: 8 Tips For Breaking Into That Senior Role

Managers who’ve been in their current position for a long time may struggle to break into senior leadership positions. While career progress of this nature can be challenging, you can take steps to increase your chances of acquiring that leadership role.

The following 8 tips will help you map out the perfect career progression plan and achieve the senior position of your dreams. 

Not quite at the managerial level? Check out our article on building an executive career path from the very beginning.

Tip 1: Position Yourself for Senior Leadership

Being a leader and working on those skills is undeniably important when paving your way to the top. However, this isn’t enough. 

You need to position yourself as a viable candidate for senior leadership. This means you’ve acquired the following:

  • Influence (over big and impactful decisions) 
  • Relationship capital
  • Some degree of power at your company

Many traditional leaders have not acquired these line items. Accomplishing them is what helps you remain top-of-mind for higher-level roles.

It’s not uncommon for aspiring senior leaders to think about career progress only in terms of their current role or skillset. Instead, broaden your scope and make sure you’re building relationships and influence across the board; you may even want to take on duties outside your direct position if they can aid in your senior career progression.

Tip 2: The Four R’s

The Four R’s are defined as: rethink, reboot, relearn, and reinvent. Why are these so essential for breaking into senior roles?

An influential leader can rethink processes to make them more efficient, reboot these processes, relearn essential skills or new strategies, and reinvent completely where needed.

Throughout your day-to-day career progress, try and achieve the following:

  • Brainstorm where there are inefficiencies and come up with solutions
  • Make everyone’s job around you better and easier (reducing inefficiencies is a crucial component to this)
  • Exceed expectations, always. The bare minimum is not your friend

Tip 3: Be Proactive

Myth: my qualifications speak for themselves, and people will call me for senior leadership interviews.

Being proactive is an essential part of making career progress towards senior roles. While many highly qualified individuals think their resume speaks for itself and people will find them, this isn’t true. 

Stewart, Cooper, & Coon discovered that CFO openings receive over 250 applications. Seek out opportunities and be prompt with your applications. Constantly review job openings that interest you, check in with your network about possible positions (more on that next), and set job alerts.

Need help finding suitable senior leadership openings? Jennings Executive can match you with the perfect role. Learn more today.

Tip 4: Stop Neglecting Your Network

Meg Guiseppi, a C-suite career strategist, remarks that far too many executive job seekers neglect their network while they’re securely employed. This is a problem because many of the best paths to senior leadership are paved with who you know, not what you know. 

One survey found that as many as 85% of roles are filled via networking, and the same is true for higher-level positions.

Career progress for aspiring senior leaders means maintaining your network and constantly seeking new connections. Check in with people, get lunch together, send birthday messages, attend networking events, and much more.

Tip 5: Avoid Being a “Jack-of-All-Trades”

One common misconception about job hunting that exists at all levels is that being a jack-of-all-trades is better than honing in on specific skills. While it’s true that senior leaders need to have worn many hats, the most successful candidates are those who focus on a particular goal.

Demonstrate in your job search that you’ve accomplished a lot, but make clear that you’re using that experience to hone in on a specific goal. Should that goal align well with the roles you’re applying for, you’ll stand out from the crowd.

Tip 6: Make Clear You’re Interested in Senior Positions

Your career progression plan needs to include express interest in senior positions. As you prepare for a career transition into one of these roles, let your manager and current leaders at the company know you’re interested in this type of leadership. 

Ask for feedback and input on what you should do to prepare for this change; let them tell you what they feel your strengths and weaknesses are. Seek guidance on what steps you can take now to further your career progress towards these higher-level roles.

Tip 7: Solve Problems Without Being Asked

Do you notice problems or inefficiencies at your current company that others are avoiding? Perhaps other people haven’t seen these issues. The pinnacle of being a high-level leader is taking the initiative and solving problems. 

Without being asked, work towards solving these issues, just as a leader would. Becoming complacent is a killer for those interested in career progress towards senior leadership. 

Even if you’re unable to solve the problem, you tried when nobody else did. Win-win. And, if you solve the issue successfully, you’re going to gain significant visibility at the company; this is essential for senior leadership consideration.

Tip 8: Work with an Executive Search Firm

Sometimes, you need the right firm to connect you with the right role. That’s where an executive search firm comes in.

Here at Jennings Executive, we have over two decades of experience placing candidates into senior roles in various industries. Don’t spend your career waiting for the right moment. Instead, let us help you find it now. Learn more!

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%.