Many years of operation do not guarantee continued success, as legacy B2Bs that call on Tiffany Lyman Otten to reposition their brands have discovered.
A legacy B2B brand often has an established customer base and industry niche, which can insulate it from losing relevance in a sharp decline. But when one does, it seems to start with friction. This is the first sign that something in the business needs to change.
Tiffany Lyman Otten is frequently called in to be that change. She has led numerous GTM resets and stabilized multimillion-dollar accounts. It is her dedication to supporting enterprise organizations through these high-stakes transitions that has solidified her legacy in the industry.
Otten works to assist long-standing and scaling B2B organizations in adjusting their go-to-market systems when these processes are struggling.
She says, “I’m brought in when things stop making sense, when numbers don’t add up, teams live different realities, and everyone is chasing the wrong metrics.”
Modernizing a long-standing brand involves more than updating branding and marketing for Otten. The issue, she has found, lies within how the business shows up, sells, and scales, which are the fundamentals of its system.
The Earliest Signal Is Not in the Dashboard
The signs of brand decay may be overlooked by boards and executives. Cues such as pipeline decline, longer sales cycles, and higher churn can typically be the indicators that inspire action, but Otten claims the earliest signals arrive sooner.
She says the signs surface through people, explaining, “I strongly evangelize talking to people that are frontline sales and customer retention, because they’re going to hear and see things that you’re not going to know in your ivory tower dashboards.”
When sales teams spend a disproportionate amount of time on training, Otten says this is a common warning sign that they are trying to overcome perception through education. In her experience, this means “somebody else is setting the perception for you.”
In practice, the market, including competitors, has begun defining the category in the brand’s place. It is Otten’s experience that this dynamic occurs when companies attempt to claim ownership of a term without backing it through operations.
Whether it is a trending marketing term like “clean,” “hydrating,” or “all-natural,” when competitors move faster than the company, they can saturate the market with content using the term. They then establish the buying criteria, and the legacy brand can keep its recognition.
Starting by Interrogating the Gaps Between Internal Truths
To reposition the brand, Otten begins by identifying the gap between how the company describes itself and how its customers experience it.
“Wherever you see the friction and the disconnect, that’s the difference between what you think you are and what your customers are saying you are,” she says.
She runs a simple diagnostic to find the difference.
Product marketing is asked to define the primary customer pain points and assign unique values to each; sales is asked the same questions, without context. Then, customer retention can be corrected, and closed-won and closed-lost customer conversations can begin.
How Otten performs this adjustment speaks to her ability to work across functions. Repositioning addresses CRM hygiene, marketing automation, sales enablement, and content strategy.
It is the operational handoffs between each, functioning in optimized isolation, that can cause organizations to rebrand and continue to underperform.
Three Moves to Turn Repositioning Into Repetition
Otten guides organizations through turning repositioning into a repeatable process in three steps, so that falling back into underperformance may be avoided.
The first move is to perform disciplined qualitative work consistently.
Otten says, “Marketing should be doing this at least once a year, maybe twice a year. It hardly costs anything; it just takes time.”
She continues, “Something can’t exist in your CRM if nobody thought to log it or create a field for it.”
With this foundation, qualitative insight may become a guardrail for decisions downstream.
Next, she suggests pairing those insights with behavioral and opportunity signals. Doing so may help leaders examine deal cycles, customization patterns, and the gap between target customers and genuine buyers.
Organizations may be aware that increasing customization can signal misalignment, and lengthening cycles may indicate a trust gap being driven by unclear positioning.
Lastly, Otten pressure-tests the Ideal Customer Profile using profitability rather than volume. This step may help determine if an organization’s chosen ICP is actually the ICP it reflects.
She advises businesses to define the best-fitting customer using long-term profitability, and ideally, the LTV-to-CAC ratio. Using this foundation, customers are stack-ranked and analyzed by their brand.
In her experience, what organizations discover based on these steps may be disquieting. A company could uncover that its largest or loudest customers do not sustain the business.
Otten recalls one agency where the baseline support effort was identical for a $7,500 monthly retainer and a $27,500 retainer. A quietly eroding margin was exposed.
Repositioning companies that ignore these metrics can amplify the incorrect demand and chase numbers that do not reflect the state of the business.
Updating the System, Not Just Cosmetics
The most common issue with legacy B2B companies Otten sees is cosmetic change without correcting structural failures.
She says, “Nobody wants to hear their baby is ugly,” and explains that companies may instead “[focus] on activities and pretty things instead of the ugly stuff.”
By “ugly stuff,” she means internal believers see the best in the company, and they make the redesign decisions from insulated think tanks.
The market, in Otten’s experience, often does not respond to purely cosmetic adjustments, because they do not address the issue. Instead, she urges teams to use scientific rigor to find solutions.
She says, “Get your hypothesis, then try to disprove it,” because without discipline cultivated through empirical interrogation, messaging can feel right internally without aligning with buyers’ decision-making processes.
Earn It: How Legacy Brands Can Recover Their Advantage
Once brands realign their metrics with their effort, the systems may grow stronger. Otten is skeptical that these future-ready brands require an all-new methodology for long-term success.
In her opinion, “A future-ready B2B brand is one that does the fundamentals best.” She says it is centered on answering customer needs in a more accurate and clarifying way.
So while the mandate of B2B brands remains steadfast, the tools at their disposal have changed. Recently, how buyers build shortlists has shifted, in part due to how AI is accelerating discovery.
Until now, brands acted as a gatekeeper. “If you’re not on the short list, you’re fighting for scraps because over 90 percent of deals go to the short list,” Otten says.
While this remains true for most categories, buyers today know they cannot keep pace with the volume of new solutions. This is a doorway for disruptors and for savvy repositioning, because when a company reframes the problem or the solution, the shortlist can expand.
For legacy brands, this could be an opening but also a risk. If competitors can redefine the category, then incumbents must reestablish buying criteria. Through Otten’s repositioning strategy, brands may align what they sell, how they sell, and what the market hears.
Her journey shows that the story of B2Bs is one of coherence over reinvention, where true success is earned through operational clarity.
