The 5 Pillars of Winning Pricing Strategies

The 5 Pillars of Winning Pricing Strategies

40-year high inflation and weakening demand are making pricing top-of-mind across all types of companies. Business leaders face pressure from boards, shareholders, and creditors to maintain short-term sales and margin plans. 

Consequently, business leaders are turning to price to manage these challenges since it’s a factor within their control.

Understanding price and how best to leverage it is critical for every company. Any organization can gather published inflation statistics for its industry and make high-level price increases on that basis, but that isn’t a long-term winning strategy. 

Best-in-class pricing strategies require a nuanced understanding of your holistic context within an industry. The following 5 pillars will help you get that detailed understanding to optimize the prices of your products and services.

The 5 Pillars For Pricing Strategy Success

  1. Monetization: Pricing monetization refers to how a product or service is packaged and billed to the customer. Monetization methods must align with how customers consume and engage with your products and services. This straightforward model is most appropriate for transaction businesses, such as retailers and wholesalers. 

Monetization is more open-ended in service and technology sectors where recurring revenue models have become the norm. While companies like their predictability, these models may not align with consumers.

Consider a corporate gifting platform or service that allows individuals to select gifts to send to customers or colleagues. Some service providers might use a recurring revenue model with a recurring “fixed’ fee” or “per user” license. However, the customer would likely view their consumption based on the number of gifts purchased. In contrast, a less tangible cloud security platform would favor recurring models. 

Customers across all industries expect pricing to align with how they consume your product.

  1. Position: Before adjusting pricing strategies, you must verify that your portfolios align with customer needs and competitors. This relationship is often based on gut feeling rather than data. 

You’ll want to empirically verify the following: Are you serving customer needs? Are you doing so at the right price points? How does this compare to competitors? Failing to validate those considerations likely means you’re losing profits.

Leading organizations conduct regular ‘outside-in’ reviews to rigorously evaluate their portfolios’ fit relative to customer needs and competitors. Such processes are conducted by cross-functional teams (sales, finance, pricing, product management, etc.) and help uncover portfolio gaps, risks, and opportunities. 

For example, price increases may be justified when a product priced equal to its competitors is found to be more valuable than them. 

In addition, a portfolio and price-band comparison can identify gaps in competitor strategies. You can then fill in those gaps to increase market share and profits.

  1. Architecture: Uniform price adjustments often underperform because organizations need to understand the nuances of their various products. Not all products carry the same price perception or sensitivity. For example, customers know the prices of staple items such as bread, milk, and bananas,  but they may not recall the prices of other items. Further, those same customers are more likely to develop perceptions of grocery stores based on the price of key-value items.

You’ll be most successful if you understand each product’s value and base pricing on that. Importantly, you want to regularly evaluate what percentage of customers buy each product and how much of a customer’s total spend that is, in addition to elasticity. Doing so helps you maximize pricing and adjust as needed.

  1. Incentives: Once organizations have the proper portfolio position and structures in place, commercial incentives (including price) must drive the intended customer behavior.

Take a SaaS solution that offers higher levels of service at higher prices. Are the incremental benefits – as compared to the most basic solution – worthwhile to the customer? Is the incremental price worth the risk to the sales team promoting and selling the solution? 

For B2C, consider TVs. Are there clear and compelling reasons to upgrade from a “great” to an “excellent” device?

Regardless of industry, aligning incentives starts with measuring item-level profit and customer preference. You can do so through A/B testing and conjoint analysis. What you discover from these analyses informs pricing and marketing tactics. 

Take the TV example above. By discounting the “excellent” TV, customers might upgrade from a “great” one and boost overall profits.

  1. Management: Many organizations take scientific approaches to establish the correct price but experience price leaks because they don’t evaluate and enforce proper discounts. 

Take a B2B organization with a well-informed list price but discounts based on something other than data. Sales teams might be incentivized to pass along discounts to avoid difficult conversations with customers, and doing so inadvertently impacts profits. Similarly, B2C retail merchants striving to hit volume quotas might overdo the use of rebates and coupons, undermining profits and brand perception.

Leave it to The Experts

Pricing strategy is an inherently challenging topic. To maximize profits, you want to create an open dialogue across pricing decision-makers and take some basic precautions to prevent profit leakage and needless oversights. 

Paramount to your pricing strategy is leaving big decisions to the experts. If you don’t yet have in-house pricing strategists, you may be leaving revenue on the table. Jennings Executive has over two decades of combined experience matching companies with pricing leaders who will help you create enduring pricing strategies that maximize profits. Learn more today!

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%.