Crafting a Modern Leadership Strategy: Building a Sustainable Culture in the Age of Remote Work

Employee Well-being and Vacation Benefits

In a rapidly evolving corporate landscape, where remote work becomes the norm and employee well-being rises in priority, effective leadership demands a fresh perspective. Modern leaders are not just tasked with steering their organizations towards financial success but also with fostering a culture that resonates with the aspirations and concerns of today’s workforce. At Jennings Executive Search, our expertise in executive recruitment across finance, pricing strategy, and professional services sectors offers us unique insights into leadership dynamics and the changing expectations of the C-suite.

The Shift in Employee Expectations

The corporate landscape is evolving, with seismic shifts reshaping what employees value and expect from their employers. Once, a competitive salary and a clear career trajectory were the hallmarks of an attractive job offer. Now, in the eyes of the modern professional, these traditional lures have been supplemented, if not surpassed, by the allure of holistic well-being, meaningful work, and a robust work-life balance.

This concept of work-life balance has evolved beyond just a fashionable buzzword—it’s now a fundamental expectation. Notably, the younger generations of employees, who are now forming the backbone of many organizations, emphasize the direct link between mental well-being and their productivity and satisfaction at work. Their preference? Organizations that not only recognize this link but actively champion a balanced professional life.

At the heart of this new paradigm is vacation time, no longer viewed simply as periodic breaks from work. Today’s employees see vacations as pivotal opportunities to recharge, follow passions, and nurture relationships outside the professional realm. Underlining this sentiment is a Glassdoor survey where a striking 57% of respondents stated that benefits and perks, especially vacation and paid time off, play a major role in their job decisions.

This transformation isn’t confined to the world of startups or tech giants. Our hands-on experience at Jennings Executive Search, working alongside investment banks, fintechs, and portfolio companies, provides a clear lens into this trend. Those organizations that have embraced progressive vacation policies, taking cues from companies like Netflix with their groundbreaking “unlimited vacation” stance, enjoy a pronounced advantage in the recruitment arena. Such policies transcend being mere perks; they symbolize a deep-seated commitment to employees’ overall well-being. It’s an approach that not only magnetizes top-tier talent but also yields tangible benefits like heightened productivity and reduced costs associated with employee health and turnover.

To summarize, as the definition of a desirable workplace undergoes this transformation, the onus falls on leadership to recognize and adapt. It’s no longer just about offering a job—it’s about fostering a culture where employee well-being is paramount, where substantial vacation time is not a luxury but a testament to an organization’s commitment to its workforce’s holistic health.

Why Vacations Matter: The Win-Win Strategy

As the dynamics of the corporate ecosystem evolve, leaders are coming to a significant realization: Vacations are not just breaks; they’re strategic investments. These periodic pauses from the hustle and bustle of work are pivotal in sustaining long-term employee efficiency and organizational growth. Here’s how vacations provide a win-win scenario for both employers and employees:

  • Boosting Productivity: Contrary to conventional beliefs, time off can boost overall productivity. A well-rested mind is more agile, creative, and driven. Instead of viewing vacations as lost workdays, leaders should see them as investments towards enhanced output. A study by Harvard Business Review highlighted that frequent vacationers reported being 30% more productive.
  • Cost-Efficiency: Employees who continuously work without adequate breaks are more prone to burnout, health issues, and decreased efficiency. Over time, this leads to higher healthcare costs for companies and even potential turnover expenses. According to the American Psychological Association, job stress costs U.S. businesses approximately $300 billion a year.
  • Strengthening Employer Brand: In today’s age of transparent company reviews and employee testimonials, a generous vacation policy can be an influential marketing tool. It sends a message about the organization’s values, making it more attractive to prospective talent. Companies like HubSpot, known for its flexibility and generous PTO, consistently ranks high on “Best Places to Work” lists.

Crafting a Culture for Today’s Workforce

In the era of digital disruptions, global connectivity, and unconventional work patterns, leadership demands an approach that’s attuned to the contemporary workforce’s ethos. This workforce, driven by millennials and Gen Z, values flexibility, inclusivity, and purpose above all. As C-suite executives, understanding and responding to these expectations isn’t just a progressive strategy—it’s imperative for organizational longevity and brand resonance. Here’s a deeper look into the foundational blocks of this modern corporate culture:

Remote Work & Flexibility: The transition to remote work is more than just a temporary solution; it’s becoming a part of the modern work ethos. Leadership today must recognize and adapt to the benefits and challenges of this model. By leveraging tools, training, and communication strategies, leaders can ensure a seamless experience for their remote teams. A Gartner survey found that 82% of company leaders intend to allow employees to work remotely some of the time post-COVID-19.

Holistic Well-being: Beyond vacations, executives should also focus on initiatives that promote mental health, continuous learning, and personal growth. Such initiatives reinforce a sense of belonging and purpose among employees.

Inclusive Leadership: Modern leaders embrace diversity, not just in recruitment but in thoughts, ideas, and problem-solving approaches. An inclusive culture drives innovation and strengthens team cohesion. Companies with inclusive leadership are 1.7 times more likely to be innovation leaders in their market, according to a study by Deloitte.

Engage with Experts for Insightful Leadership Strategies

At Jennings Executive Search, we specialize in understanding the intricacies of modern leadership demands, especially in sectors like private equity, fintech, and professional services. Whether it’s crafting a sustainable remote work policy, integrating IT analytics, or devising a merger strategy, we offer insights backed by deep industry knowledge.

For executives looking to navigate these transformative times effectively and build a sustainable culture that resonates with today’s workforce, our expertise stands unparalleled. Engage with us to redefine leadership for the modern age.

Conclusion

The leadership playbook is undergoing a profound transformation. In an era defined by digital innovation, remote work, and evolving employee expectations, executives have an opportunity to pioneer a new age of leadership. By integrating holistic well-being into organizational culture, valuing the balance between work and relaxation, and promoting inclusivity, modern leaders can craft a legacy that stands the test of time.

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%.