What to Do (and Not Do) When the Strategy Starts Working

At the beginning, the problems are visible. Performance is down. The system is under strain. Priorities are clear because they have to be.

The more dangerous moment comes later - when the strategy begins to work.

The numbers start moving. The team feels momentum. Leadership sees proof that the reset is landing. It finally feels as though the hardest part is behind you.

This is the moment every turnaround is working toward. It is also the moment where the next decision matters most. Because once a strategy starts to show traction, the instinct is almost always the same: double down.

Sometimes that is exactly the right call.

But before any organization does that, there is a hidden step that needs to be taken - one that is easy to skip precisely because the results are real and the excitement is justified.

That step is not asking whether the strategy is working. It is asking whether this is the best possible version of working.

Before scaling success, leadership has to reassess it. Not because the early strategy was wrong, but because once traction appears, the decision changes. The question is no longer whether the turnaround can create growth. It becomes whether the growth being unlocked is the most durable, highest-return, and system-strengthening growth available.

That means pressure-testing a few things that are easy to overlook in the glow of early progress.

• Is this the right success, or simply a success?
  Is it durable, or does it rely on conditions that may not hold? 
• What will it take to sustain? 
• What will it cost to scale? 
• How does it interact with the core business? 
• What second-order risks sit underneath - brand tension, audience conflict, channel distortion, retention weakness, or operational strain? 
• And just as importantly: are there alternative growth paths that may be less visible, but more valuable?

At a practical level, this shows up through questions like:

• What is the lifetime value of the new audience relative to its acquisition cost?
• Does this growth reinforce the core business, or compete with it?
• Is retention strong enough to justify deeper investment?
• Is the brand becoming more resilient as it grows, or more fragile?
• Are there adjacent audiences or levers that could unlock more value with less risk?

That step is often compressed or skipped, not because teams are careless, but because success creates confidence, and confidence makes the next move feel obvious.

That is exactly what happened with Woodbridge.  

We had done what leadership had asked. We had successfully unlocked penetration with Zillennials - an audience the brand had struggled to win for years - and the business had returned to outperforming the category. The strategy was working. The results were real. And because the original objective had been to grow younger, the most natural conclusion was that the next step was to accelerate in that direction.

It was easy to see why that success carried so much weight.

Zillennials were the hardest audience to unlock. They had historically rejected the brand. They had a weaker natural fit to Woodbridge’s price point and to the mainstream wine category overall. They were also being aggressively courted by brands like Barefoot, which had a more obviously youthful tone, more resources, and stronger superficial relevance from the outset. Against that backdrop, the fact that Woodbridge had begun to gain traction with them was not incremental progress. It was strategically impressive progress.

Which is exactly why it was so important to pause.

What should have happened next was straightforward in theory, even if difficult in practice. The business should have assessed whether this new growth path was the most valuable one available. It should have asked what would be required to sustain it, whether it could compound efficiently, how it interacted with the core buyer base, and whether other audiences might offer greater long-term value at lower risk. In other words: not whether the Zillennial strategy had worked, but whether it was the best growth path to keep scaling from there.

That step was overlooked. Not because the team failed. In many ways, it was overlooked because the team had succeeded.

Once an organization decides it does want to continue along a given growth path, the next principle is deceptively simple: 

If the strategy is working, let it work.

That does not mean standing still. It means compounding carefully. It means optimizing within the logic of the strategy already in market. It means protecting the signals that are creating traction. And it means resisting the temptation to introduce a new, untested engine simply because the first one has finally begun to turn.

Because scaling a strategy is not just about doing more of it. It is about doing more of it in a way that strengthens the system rather than strains it.

That is where the Woodbridge story turns. 

In September 2022, after the brand had started to gain real traction, I was given a top-down mandate to pivot away from the media strategy I had built - and which had been working - and instead pilot an experimental brand-performance hybrid model with a new agency. The approach had not been tested on any brand in Constellation’s portfolio. It was designed to generate high volumes of trend-driven, performance-oriented creative and accelerate younger-buyer growth through a more culturally native, faster-moving content system.

At a high level, the logic seemed reasonable. The brand had finally begun to unlock younger buyers. Leadership wanted to accelerate that progress. The proposed model came from people who were highly credible in their field and who appeared to have a modern answer for how to push momentum harder. From where I sat as the operator on the business, the risks were obvious.

The brand had only just begun to rebuild credibility with Zillennials, and it had done so by being modern and welcoming without becoming inauthentic. The proposed model leaned heavily into low-production, meme-driven, TikTok-native creative - exactly the kind of work that could feel performative rather than real for younger buyers, while simultaneously reading as low-quality and off-brand to Woodbridge’s core A55+ base. Just as importantly, the economics were concerning. The production and agency fee structure would consume a disproportionate share of the total media budget, leaving too little working spend to achieve the reach and frequency required to scale the assets that actually performed. And the timing was especially risky: the pilot would kick off in Q3 right before the critical OND holiday period when the brand needed its media to work hardest.

I built and presented a data-backed case against moving forward. My analysis showed that the production and agency costs would push non-working spend far above best-in-class levels, that the testing structure would absorb too much of the budget, and that the model would put Woodbridge at serious risk of losing share of voice during its most important selling season - precisely when Barefoot was flooding the market with more than $19M in NFL-backed media support.

Leadership moved forward anyway. I aligned and executed, but I stayed deep in the data and designed a match-market test in parallel so I would be ready to evaluate the model at the earliest possible point.

The breakdown appeared quickly.

Very few assets cleared the thresholds needed for scale. That meant we were consuming more budget than expected while generating less reach, less voice, and less real market presence. As part of the testing process, the new agency insisted on posting assets organically on the brand’s social channels to gather additional signals. The content underperformed there as well. Engagement weakened. Followers declined. At the same time, I saw the business-level effects I had feared beginning to show up in the numbers. Retained A55+ buyers softened in frequency and units per trip. Zillennial buyer growth, which had been improving under the original strategy, slowed and then stopped.

The reason was not complicated.

The creative was not working with younger buyers because it felt inauthentic to the brand. And it was not working with core buyers because it made Woodbridge look lower quality, less relevant to them, and less like the brand they knew. What had been proposed as an accelerant was, in practice, weakening both ends of the system at once.

The match-market test confirmed it. The original strategy delivered a 45% higher ROI, and its creative was 50% more effective. The new model barely cleared breakeven and underperformed effectiveness benchmarks by 18%. Even where it generated engagement signals, that engagement did not translate into purchase behavior. By the four-week mark, I had enough conviction to begin preparing the case to stop the pilot, and after Thanksgiving I was able to secure alignment from the division president to return to the original approach.

Media shifted back in January 2023.

But by then, the damage was done.

Woodbridge had effectively gone dark on national media for much of Q3 while Barefoot dominated market attention and physical merchandising through its NFL spend. Share of voice collapsed.

Merchandising share deteriorated, including in markets where Woodbridge had local NFL team sponsorships of its own. The three new product lines we had just launched into fast-growing, younger-skewing segments - Sparkling Infusions, Fruitful Blends, and Sessions - were supposed to receive dedicated support in Q3 and Q4, but the creative designed for them never meaningfully scaled, leaving all three to enter market largely unsupported. Zillennials, who had finally begun to come into the franchise, stopped growing and began to churn. Core Boomers felt the brand had changed in a way that no longer fit them and no longer signaled quality, and they began to pull back as well.

This kind of mistake is more common than it appears. Sometimes it happens quickly and visibly, as it did here. Sometimes it creeps in more gradually over time, as brands stretch too far from the system that made them work in the first place. Either way, the underlying pattern is the same: progress creates excitement, excitement creates overreach, and overreach weakens the very system that had started to recover.

In some cases, that leaves a business in a worse position than where it began.

That was the position Woodbridge was now in.

The brand had already been under pressure from a declining category, premiumization, and private label expansion. Its economics were deteriorating. Its 1.5L core, which represented 76% of depletions, was being cannibalized by its own 3L format - a COVID-era corporate launch that had become negative gross margin while stealing buyers from the profitable heart of the business. Gross margin had fallen from 38% to 24% in two years. The budget was shrinking along with net sales. And now, on top of all of that, the business had to recover from a failed acceleration that had damaged both the core franchise and the new audience it had worked so hard to unlock.

This was no longer a matter of optimization. It was a second turnaround.

I started by building the analytical foundation required to reset the business correctly. I pulled and analyzed multi-year IRI syndicated data, panel data, media spend, MMM results, internal financials, competitor data, DMA-level merchandising performance, and channel-specific trends. I decomposed an $18.4M decline into base, NPD, and incremental components, then further isolated the relative impact of velocity, distribution, NPD, and merchandising. I traced the 3L box’s cannibalization path, quantified switching volume, modeled elasticity and price increase scenarios, mapped profitability by format, and built alternative financial trajectories through FY27 that showed how the business could hold topline while materially improving margin through mix shift.

That work surfaced several critical insights. First, the brand’s most important issue was penetration, not loyalty. Woodbridge lagged major competitors in household penetration but led them in buy rate. People who entered the franchise stayed and spent. The problem was not that the brand failed once people got in. It was that not enough of the right people were entering in the first place.

Second, the Zillennial growth story - while real - was not the highest-value path forward. When I stepped back and examined category buyer data, brand funnel metrics, lifetime value, and acquisition cost by generation, the picture changed. Gen X represented a much larger and more attractive opportunity: higher spend, higher LTV, stronger baseline brand awareness, lower acquisition cost, and more natural overlap with Woodbridge’s Baby Boomer core. It was the rare growth segment that allowed the brand to get younger without behaving younger in a way that alienated its base. When I modeled the opportunity, Gen X represented roughly a $50M upside—28% larger than Millennials and Gen Z combined.

Third, the sports sponsorship strategy that the sales organization was heavily invested in had stopped working. Barefoot’s national NFL sponsorship had changed the game. I proved month-by-month and DMA-by-DMA that Woodbridge’s local team deals were no longer protecting share or merchandising position, and that non-sponsored markets often performed better. The strategy was consuming millions of dollars in largely non-working spend without delivering the commercial advantage it once had.

Fourth, the long-range plan was structurally flawed. The business was drifting into the wrong mix. Unprofitable 3L was growing while margin-accretive platforms remained too small. The path to profitability was not going to come from cost reduction or broad-based price increases. It had to come from changing what the brand sold, where it sold it, and whom it sold it to.

From there, I built the recovery plan.

I created a new portfolio architecture that separated the business into Core, Scalable Innovation, and Tactical Innovation - giving leadership a way to deprioritize the 3L box without triggering a politically difficult discontinuation conversation. The core business received the bulk of resources and the mandate to protect share. Scalable innovations like Sparkling Infusions and Fruitful Blends were prioritized for future growth. Tactical formats like 3L and Sessions received no dedicated investment and were positioned to ride brand halo only. That framework made the business sharper strategically and more rational economically.

I also challenged the division-wide targeting mandate. Rather than continue prioritizing Zillennials simply because we had finally unlocked them, I presented a rigorous case for shifting the primary growth focus to Gen X. The analysis was analytically irrefutable: Gen X had materially better LTV/CAC economics, stronger brand fit, and a much larger revenue opportunity. Leadership aligned, and that shift allowed the brand to keep broadening its shoulders younger while doing so in a way that strengthened, rather than strained, the franchise.

On the brand experience side, I replaced the sports sponsorship strategy with seasonal, retail-driven programs built around wine consumption holidays and cross-category partnerships that created real value for retailers and consumers. Instead of spending against baseball and hoping for borrowed relevance, the brand redirected more than $4.5M of non-working sponsorship dollars into programs that drove basket size, merchandising support, and volume in moments that actually mattered for the category. That pivot alone helped drive a 6% lift in merchandising-attributable sales and a two-point gain in merchandising share.

I redesigned the distribution strategy with channel-specific growth roles, built a benchmark system that used competitor velocity to establish fair-share distribution targets for growth SKUs, segmented markets into tiers based on size, opportunity, and economics, and developed explicit merchandising standards to protect the core business and reduce internal cannibalization.

And critically, I did the work required to make all of this real inside a large organization. I built the plan independently, pre-aligned cross-functional partners before bringing it to the senior leadership team, and translated controversial recommendations - moving off sports, deprioritizing 3L, shifting away from the corporate-mandated growth target - into a language the business could act on. The result was not just approval. It was authorization to begin implementing the strategy immediately.

The recovery worked.

The Gen X audience shift drove approximately three million new buyers in a year and increased core retention by roughly 11%, validating the thesis that the brand could grow younger without compromising older. The brand experience pivot reversed the losses sustained during the Barefoot NFL onslaught and materially improved budget efficiency within a shrinking envelope. The broader plan realigned the business around the levers that actually created value rather than the ones that were easiest to defend politically.

This was the deeper lesson of Woodbridge.

The first turnaround proved that the brand could unlock growth.
The second proved that growth alone is not the end of the decision.

What matters next is whether the growth is durable, high-return, and strengthening the system beneath it. That is the hidden step many businesses skip. Not because they are careless, but because success is seductive. Once something starts working, it becomes very easy to assume the job is to push harder in the same direction. Sometimes that is right. Often it is incomplete.

The better question is always the harder one: Now that this is working, what is the best version of working from here?

That is the question that separates tactical wins from durable turnarounds. And answering it correctly is often what creates the most value of all.