I have never really taken no for an answer, in fact I see it as a buying signal. This is a mindset I have pushed forward to my entire team – that nothing is insurmountable, there is always a route through, you just need to find it.
Not all great careers begin with a five-year plan and a clear destination. Sometimes the most influential leaders emerge from unexpected detours, where initial dreams give way to discovered passions that change entire industries. Cherisse Jameson’s journey from aspiring stills photographer in Cape Town to one of the most innovative forces in B2B technology marketing exemplifies how embracing the unexpected can lead to extraordinary impact.
Twenty-seven years ago, a reluctant return to England became the catalyst for a career that would redefine how technology companies connect with their audiences. What began as a temporary stop to save money for a return ticket to Cape Town transformed into a leadership journey that has shaped digital transformation across the IoT, telecommunications, and AI landscapes.
“My journey began by accident really,” Cherisse reflects on those early days. “I thought I had found my long-term passion in photography. The rest, however, as they say, is history.”
That history tells a story of remarkable intuition, relentless innovation, and an unwavering belief that authenticity drives business success. From becoming the youngest field sales manager in her publishing company’s history at just 18 years old, complete with company car and petrol card, to being shortlisted in the final two for The Drum Awards as a Business Innovator, Cherisse has consistently challenged conventions while delivering exceptional results.
Her approach to business development goes beyond traditional sales tactics. It’s about understanding pain points, building genuine relationships, and creating solutions that transform how technology brands engage with decision-makers. In an industry often criticized for prioritizing metrics over meaning, Cherisse has built a reputation for campaigns that deliver both commercial results and authentic human connection.
THE FOUNDATION: LEARNING TO LISTEN, LEARNING TO LEAD
Cherisse’s early success in classified sales for a prestigious publishing house in the 1990s provided more than just career momentum. It revealed a natural talent for understanding what businesses truly need and translating that understanding into solutions that drive growth.
“I found myself really enjoying the landscape of B2B advertising sales – the research, the solution sell, the customer rapport, the thrill of closing well thought-out, bespoke deals that matched client’s needs,” she recalls. “Having an impact on a company’s growth and goals, I found incredibly rewarding.”
This client-centric philosophy, formed in those formative years, would become the cornerstone of her leadership approach. But it was the leap she took 27 years ago that truly defined her trajectory. When headhunted to join a start-up publishing company in the tech space with former colleagues, Cherisse chose risk over security, potential over certainty.
That decision to join what she describes as “something quite special” proved transformative, not just for her career but for the countless technology brands she would help elevate over the following decades.
DEFINING MOMENTS: WHERE IDEAS MEET IMPACT
Ask Cherisse about the moments that shaped her leadership philosophy, and she points to something fundamental: seeing ideas come to fruition. In a business environment where many leaders focus on process over outcomes, Cherisse has maintained an unwavering focus on results that matter.
“I think when you really listen to market needs and react accordingly, you see solutions meeting business pain points head on,” she explains. “This is what really motivates me. I have been fortunate enough to see this happen many times over the years.”
Her approach to challenges reveals a mindset that has become integral to her team’s culture. She has never accepted “no” as a final answer, instead viewing it as what she calls “a buying signal.” This perspective transforms obstacles into opportunities and rejection into deeper engagement.
“I have never really taken no for an answer, in fact I see it as a buying signal,” Cherisse emphasizes. “This is a mindset I have pushed forward to my entire team – that nothing is insurmountable, there is always a route through, you just need to find it.”
This philosophy has manifested in countless innovations throughout her career. From creating in-person networking events and creative video solutions on show floors to building analyst and influencer partnerships, lead generation campaigns, and expert nurturing initiatives, Cherisse has consistently found routes where others saw roadblocks.
Her legendary work ethic underscores this approach. In her early career, she set a company record by making over 250 calls in a single day and regularly logged over 10 hours of phone time per week. But this wasn’t about volume for its own sake. It was about understanding a fundamental truth that still drives her success today.
“I was never shy of the phone and it taught me a vital lesson early, that this really is key to making a success of yourself,” Cherisse reflects. “People buy people and hiding behind email will only ever get you so far.”
THE AGILITY ADVANTAGE: REBUILDING BOXES INSTEAD OF FITTING INTO THEM
One of Cherisse’s most valuable leadership lessons centers on flexibility and responsiveness. In an industry where companies often try to force client needs into pre-existing service packages, she has built her reputation on doing the opposite.
“Don’t try to fit your clients’ needs into your own purpose-built box,” she advises her team. “Knock the walls down and always be ready to lift and shift the original plan to something entirely different if the conversation or need takes you there.”
This agile approach has proven particularly valuable working across multiple dynamic brands under WeKnow. Rather than maintaining rigid structures that limit possibility, Cherisse has fostered an environment where innovation thrives through adaptability and strategic pivoting.
Her work to identify and partner with nearly 20 of the world’s leading independent analysts, journalists, and influencers in the IoT, telecommunications, and AI space exemplifies this strategic thinking. What began as extensive research evolved into a mission to build genuine relationships with industry opinion makers.
“I made it my mission to become friends,” Cherisse explains. “Now years later, these leading independent opinion makers are partnered with us for exclusive projects that are made available to my clients. It immediately changed the face of our business.”
This stable of expertise, readily available for exclusive client projects, represents something unique in the B2B technology marketing landscape. It’s not just about access to thought leaders but about integrating their perspectives into campaigns that carry genuine authority and credibility.
THE WEKNOW DIFFERENCE: TIME, TALENT, AND TRANSFORMATION
When asked what sets WeKnow apart in connecting B2B hi-tech clients with their target audiences, Cherisse points to something that cannot be manufactured or accelerated: time in the space.
“There is nothing that can compare to growing up with the industry and seeing 27 years of digital transformation across a value chain,” she observes. “As a media house, reacting to this transformation accordingly and providing the solution that fits the need, has been what we have always tried to achieve.”
But longevity alone doesn’t create distinction. Cherisse credits WeKnow’s success to several interconnected factors. An exceptionally dedicated team that goes above and beyond for every campaign. A commitment to quality, business-focused, opinion-led content that serves the community. Strategic partnerships with not just thought leaders but over 100 leading global events.
And underlying it all, a philosophy that remains constant regardless of technological change: “Content will always be king!”
This belief in substantive content creation has positioned WeKnow head and shoulders above competitors who prioritize quantity over quality or flashy tactics over meaningful engagement. In an era of information overload, Cherisse has built a business model centered on creating content that decision-makers actually want to consume because it genuinely informs their strategies.
CREATIVITY MEETS DATA: THE RECIPE FOR CAMPAIGN SUCCESS
The tension between creativity and data-driven strategy challenges many marketing leaders. Cherisse has resolved this tension by refusing to choose sides, instead using both in equal measure.
“I heard a great saying the other day,” she shares. “The best way to predict the future is to create it. I love this.”
Her approach integrates creative thinking with rigorous analysis. Who is reacting to what content and why? Which campaigns failed and which ones succeeded? What ingredients led to success and what elements should be eliminated? Using these insights, combined with what she describes as “a huge sprinkle of creativity,” Cherisse drives ideas to market that deliver measurable results while maintaining the human appeal that technology marketing often lacks.
The visual component of this strategy cannot be understated. In an environment where audiences make snap judgments about content value, WeKnow’s creative team plays an integral role in campaign success.
“You have 11 seconds to visually draw in an audience, so what our creative team deliver is integral to a campaign’s success and can directly optimize results,” Cherisse explains. “We are all consumers at the end of the day. Are we going to be drawn to basic black and white, text-heavy assets, or do we need to be inspired by what we see?”
This understanding that B2B audiences are still human beings making decisions based on emotional engagement as much as rational analysis distinguishes WeKnow’s approach from competitors who treat technology marketing as a purely logical exercise.
NAVIGATING COMPLEXITY: THE DARK ART OF PERFECT TIMING
The IoT and telecommunications IT landscape presents unique challenges that require sophisticated understanding of vertical markets at different stages of technology adoption. Cherisse describes one aspect of this work as “a dark art”: engaging the right persona with the right message at the right time.
Rather than attempting to serve all audiences equally, WeKnow has embraced specialization. “We quickly found that you cannot be all things to all people,” Cherisse notes. “Find your niche and go after a select audience. Don’t be the jack of all trades, be the master of one.”
This focus has led to deep expertise in understanding how different sectors need to be approached and engaged. But perhaps Cherisse’s most important insight concerns lead generation, an area where many technology companies waste significant marketing spend pursuing short-term results.
“It is not a one-hit wonder. This is short-sighted and ultimately a waste of marketing spend,” she emphasizes. “Every campaign, regardless if you are a leading blue-chip in tech, needs a long-term view when it comes to lead generation. Nurturing your audience with your expertise and solutions is absolutely key.”
This perspective requires what Cherisse describes as humility in business. Even well-known technology brands cannot assume their reputation alone will drive engagement. Audiences need constant reassurance that investing in a particular product or partner represents the right decision.
“You need to constantly pivot your messaging and outreach to reassure your target audience you are, without any doubt, the right choice for their business and showcase exactly why,” Cherisse explains. “Even when engaging with the highest level of persona, executives need to be reassured that their investment is being put in the right hands.”
THE ELITE CAMPAIGN: A MILESTONE IN STRATEGIC INNOVATION
Among Cherisse’s many innovations, one stands out as a defining achievement: the creation of what WeKnow calls Elite Campaigns. These comprehensive initiatives directly address a fundamental business challenge that every technology company faces.
“Ultimately whoever you are, whatever solution you are selling, if you have invested budget, you need ROI,” Cherisse states plainly. “ROI in B2B publishing equates to interested, engaged leads, but to achieve this outcome you need thought leadership, strategic brand awareness, and only then can you achieve targeted lead generation.”
The Elite Campaign structure embodies this progression. It begins with endorsement from an industry-renowned analyst who interviews an executive to set the campaign’s context. This is followed by release of a business-focused report discussing challenges in a particular space and how specific solutions address them. The report, analyst-written but sponsor-steered, creates what Cherisse calls “a winning combination to engage a high-level persona.”
The campaign culminates in an industry roundtable where experts discuss how their companies’ solutions address pain points, ideally alongside customers who can provide real-world implementation examples. This structure transforms traditional marketing into genuine thought leadership that decision-makers seek out rather than avoid.
The Elite Campaign has become WeKnow’s most successful package sold across the business, validating Cherisse’s fundamental belief that effective marketing serves audiences by informing their decisions rather than simply promoting products.
BUILDING TRUST IN A COMPETITIVE DIGITAL ENVIRONMENT
In today’s fast-paced digital landscape where competition for attention intensifies daily, Cherisse maintains that face-to-face connection remains invaluable. She seizes every opportunity to meet people in person, understanding that human connection creates trust in ways that digital communication alone cannot replicate.
“Don’t underestimate the need for humans to be together to really do business well,” she emphasizes. “Stand out from the crowd, don’t be afraid to show your personality!”
Her approach to client engagement involves multi-channel persistence designed to demonstrate serious intent. Rather than accepting a single unreturned call or email as rejection, Cherisse approaches targets from multiple angles to create what she calls FOMO: fear of missing out.
“If they don’t pick up the call to you, what potential opportunity could they be missing?” she asks. This mindset transforms outreach from an interruption into an opportunity for the prospect, reframing the entire dynamic of business development.
STORYTELLING: THE BACKBONE OF TECHNOLOGY MARKETING
Despite working in corporate technology sectors populated by serious professionals focused on technical specifications and business outcomes, Cherisse maintains that basic principles of consumer engagement still apply. At the heart of these principles lies storytelling.
“Really this is everything,” Cherisse states. “The backbone of a successful campaign is the positioning and storytelling. Just because I sit in a corporate industry with lots of serious people within it doesn’t mean that the basic rules of consumer engagement don’t apply.”
Her storytelling approach follows a staggered structure: create the story and paint the picture, tackle real-world business pain points, and once the audience is engaged, reveal the solution. This narrative arc transforms marketing from product promotion into problem-solving, positioning technology vendors as partners in addressing business challenges rather than simply suppliers of tools.
This storytelling philosophy extends to how WeKnow’s creative and strategy teams collaborate. Ongoing communication ensures that client objectives and existing brand values align with expert content and visually compelling assets. The result is campaigns that seamlessly integrate substance with style, information with inspiration.
DEFINING EFFECTIVE LEADERSHIP IN A DIGITAL-FIRST WORLD
When asked what qualities define effective business development leadership in today’s digital ecosystem, Cherisse emphasizes grounded understanding over confident assumption.
“Not pontificating your own thoughts and opinions without real insight and data,” she begins. “Take the time to get under the skin of the industry you are serving, ask the difficult questions, understand what people are struggling with, and do this in a personable, meaningful, and respectful way.”
This approach builds rapport with clients, earns respect from peers, and provides crucial insights into market needs that inform commercial strategy. It’s leadership rooted in curiosity and service rather than ego and hierarchy.
Cherisse fosters innovation within her teams by encouraging them to identify campaigns that stand out and understand why those campaigns resonated. By integrating the exciting, dynamic, and innovative elements of various successful initiatives, WeKnow continually evolves its offerings to reflect best practices across the industry.
“I also ask people why they like certain people, encourage free-flowing conversation with your team about these things,” Cherisse explains. “It allows you to really understand each other and how each other ticks. It ultimately gets the best out of the people around you to know what appeals to them most.”
STAYING AHEAD: ADAPTATION AS COMPETITIVE ADVANTAGE
In an environment where technology and consumer behavior constantly evolve, maintaining relevance requires vigilant observation and rapid adaptation. Cherisse watches closely what’s happening at the market’s forefront, identifying opportunities to create similar but superior solutions.
But her definition of success extends beyond conventional performance metrics. While many in her industry focus exclusively on engagement rates, click-throughs, and pipeline metrics, Cherisse measures success by a more fundamental standard: business deals done.
“This is the end goal for everything invested,” she states. “We want our clients to win business and see us as the vehicle that enabled that win, or even better, wins!”
This outcomes-focused approach keeps WeKnow aligned with what actually matters to technology companies rather than vanity metrics that look impressive in reports but don’t drive revenue.
Looking ahead, Cherisse sees IoT and AI as forces that will drive all aspects of human life into the next era of existence. This makes the partnership decisions her clients make integral to their competitive positioning.
“If they get it right, it stands them apart from competitors,” she observes. “Their offering, solutions, and expertise come together to offer the world a seamless end-to-end solution to drive transformation.”
THE DISCIPLINE OF SUCCESS: BALANCING MULTIPLE BRANDS AND PRIORITIES
Managing multiple brands and platforms while maintaining high performance across all initiatives requires exceptional discipline and strategic prioritization. Cherisse has developed a personal system that begins before most people wake.
“My biggest life hack is getting up at 5am every day to get ahead of my daily needs without stress,” she reveals. This early start provides space to prepare mentally and strategically before the workday’s demands intensify.
But it’s not just about working longer hours. Cherisse recognizes that sustainable performance requires physical and mental health as foundations. “Being healthy in your body is directly related to productivity in the workplace,” she explains. “I eat well, exercise daily. I get my mind and body focused and ready before the working day begins.”
Sleep represents another non-negotiable element of her performance strategy. Seven to eight hours nightly provides the recovery necessary to run at full capacity during 10- to 12-hour workdays that characterize her role.
This holistic approach to performance management enables Cherisse to maintain the intensity and focus required while avoiding the burnout that claims many leaders in demanding roles.
ADVICE FOR ORGANIZATIONS: LETTING GO TO GROW
When advising organizations looking to strengthen their digital brand presence in the B2B technology sector, Cherisse offers counsel that many executives find uncomfortable: sometimes you need to throw everything in the bin and start from scratch.
“You have to let go to grow,” she states. “Don’t be afraid to throw it all in the bin and start from scratch. Sometimes this is exactly what’s needed.”
This willingness to abandon approaches that aren’t working, regardless of sunk costs or organizational inertia, reflects the same agility she brings to client campaigns. But transformation requires more than just strategic pivots.
“Have the right team around you to make your aspirations a reality,” Cherisse emphasizes. “Never say never.”
These simple words encapsulate a leadership philosophy that has driven her success: surround yourself with exceptional people, maintain openness to possibility, and refuse to accept artificial limitations on what can be achieved.
LEADING BY EXAMPLE: EMPOWERMENT THROUGH AUTHENTICITY
As a woman leading in the technology and digital domains, Cherisse’s approach to mentorship centers on demonstration rather than declaration. She believes in rolling up sleeves and doing whatever’s needed to drive company success, modeling the work ethic and commitment she hopes to inspire in others.
“Lead by example,” she advises. “Do not be afraid to roll your sleeves up and do anything and everything that’s needed to make your company a success. Be humble, hardworking, and empathetic to those around you.”
But she also recognizes a fundamental truth about leadership sustainability: if your team and clients don’t genuinely like you, those relationships remain short-lived. The same principle that drives client relationships applies internally.
“People buy people,” Cherisse reminds us. “This rule applies with clients and internally within your own business. Be someone your team and peers aspire to be like, and this creates drive and encourages productivity.”
Interestingly, Cherisse resists the traditional leadership label, preferring to position herself as an integral part of the team rather than above it. “I don’t really see myself as a leader,” she reflects. “I prefer to position myself as an integral part of our team. If I inspire someone along the way, then fantastic, as I am inspired daily by my exceptional team.”
This humility doesn’t diminish her influence. Instead, it amplifies it by creating an environment where collaboration thrives and team members feel valued as essential contributors rather than subordinates executing someone else’s vision.
Her personal mantra extends beyond professional contexts: be kind always, as you never know what someone may be going through behind closed doors. This empathy, combined with the patience, understanding, flexibility, and humility she values, creates a leadership approach rooted in recognizing shared humanity.
“I have learned that we are all human,” Cherisse observes. “Despite the oncoming unknown of how AI will affect every walk of life, I am a firm believer that humans need humans to be the best version of themselves, to create, to build, to drive forward. We are still the future, and in order to build a better future for us all, we all need to have patience, understanding, kindness, flexibility, and humility.”
THE CRUCIBLE: THRIVING THROUGH CRISIS
When asked about her proudest professional achievement, Cherisse points to a period that tested her resilience like never before: keeping WeKnow afloat throughout the COVID-19 pandemic while the entire company was furloughed.
For approximately six months, the entire industry shut down operations. Cherisse remained in place, fighting to survive in what she describes as “the winds of the unknown.” The experience taught lessons that transcend crisis management.
“It taught me to trust the process, as my husband always says,” Cherisse reflects. “To be resilient, consistent, and hardworking even in the face of despair sometimes. To be unflappable and try not to stress over things you simply can’t control.”
This mindset proved transformative. When her team returned, they came back to brands that hadn’t just survived an unprecedented global crisis but had actually thrived. That outcome didn’t happen by accident. It resulted from the same principles that have driven Cherisse’s entire career: refusing to accept defeat, finding routes through apparently insurmountable obstacles, and maintaining focus on what truly matters regardless of circumstances.
The pandemic experience reinforced what Cherisse has always known: collaboration and partnership provide the foundation for long-term business sustainability. Her answer when asked about this topic? “Utterly vital.”
A VISION FOR THE FUTURE: BECOMING THE MUST-VISIT PORTAL
Looking ahead, Cherisse envisions WeKnow becoming the essential resource for business strategists on their procurement journey. She wants the company’s brands to serve as the point of reference for all decision-makers before they make investments.
“I want our brands to be THE point of reference for all decision makers before they make their investments,” she explains. “To be informed, inspired, entertained at times, and learn something new along the way.”
This vision aligns perfectly with her career-long commitment to serving audiences by helping them make better decisions rather than simply promoting vendors. It positions WeKnow not as a marketing platform but as a trusted advisor that decision-makers actively seek out.
But Cherisse also acknowledges a personal challenge that accompanies her professional ambitions. “I would like to find a way to not have my foot flat to the floor each day, to find a bit more balance between life and work,” she admits with characteristic honesty. “But somehow, I think this will be my biggest challenge to date.”
This candid acknowledgment reflects the same authenticity that characterizes her entire approach. She doesn’t pretend to have achieved perfect work-life balance or claim that success comes without sacrifice. Instead, she honestly shares the ongoing tensions that accompany ambitious professional goals.
THE LEGACY OF AUTHENTIC LEADERSHIP
Cherisse Jameson’s influence on B2B technology marketing extends far beyond the campaigns she has created and the deals she has closed. Her legacy lies in demonstrating that authenticity, empathy, and genuine service to clients create more sustainable success than tactics focused solely on short-term gains.
In an industry that often prioritizes automation over human connection, metrics over meaning, and volume over value, Cherisse has built a career proving that people still buy from people. That relationships matter more than transactions. That understanding what clients truly need and genuinely helping them succeed creates loyalty that no amount of clever marketing can replicate.
Her journey from reluctant returnee to England to influential leader in technology marketing shows how embracing unexpected paths can lead to profound impact. Her willingness to work harder than anyone else while maintaining humility and kindness demonstrates that success doesn’t require sacrificing values or relationships.
As technology continues transforming how businesses connect with audiences, leaders like Cherisse provide essential guidance on maintaining human elements that drive genuine engagement. Her insistence that humans need humans, even in an AI-driven future, offers important perspective for an industry sometimes too eager to automate away the personal connections that make business relationships meaningful.
The accidental beginning of her career turned out to be anything but accidental. It was preparation for leadership that would influence how technology companies tell their stories, engage their audiences, and measure their success. Cherisse Jameson didn’t plan to become a transformative force in B2B technology marketing. She simply showed up every day, worked harder than required, stayed curious about what clients truly needed, and built solutions that genuinely served them.
Sometimes the most influential leaders are those who never set out to lead but who inspire others simply by doing exceptional work with integrity, energy, and authentic care for the people they serve. That’s the essence of Cherisse Jameson’s leadership, and it’s why she’s not just influential today but will continue shaping the future of technology marketing for years to come.
