Memo: El estado de la replanificación

There was a time when a migration felt like a well-paid indulgence — a big check to a development partner, six to nine months of JIRA tickets, and a board slide that read “future-proofed.” For most brands, that future turned out shorter than promised.

Today, re-platforming is no longer just about fresh code or a prettier checkout. It’s about the real calculus of gross margin, agility, and who owns your pace of change. For the first time in a decade, more brands are migrating with unit economics and agility at heart—from big, bespoke builds to leaner SaaS stacks with just enough firepower.

I’ve sat across dozens of negotiation tables and Slack threads about this, from São Paulo to Singapore. Here’s what I see in the data, the RFPs, and the bruised forecasts.

Why Brands Replatform (Again)

For brands north of $10 million, the original replatform often happens in the sophomore phase: they outgrow Shopify Basic, build out an ERP, maybe tack on a custom frontend for conversion lifts and marginal site speed gains. Three years later, that headless stack feels less like a Ferrari and more like a third car gathering dust — costly to maintain, awkward to tune, and a liability when marketing needs a landing page live by Friday.

The drivers are universal:

Trigger Why It Matters
Total Cost of Ownership (TCO) Internal dev teams + external retainers + technical debt → draining gross margin.
Speed to Deploy A good idea loses value if it takes two sprints to ship.
Multi-channel Reality DTC-only dreams collide with B2B, pop-up retail, marketplace diversification.
M&A or PE Rollups Consolidation favors fewer systems, not more.

Where They’re Going: Patterns in the Data

Migrations are not evenly distributed. Some are gravity wells, pulling brands back to the center of mass. Some are exit ramps from legacy stacks to a place where marketing can breathe.

Here’s the snapshot:

Migration Observed Trend Rationale
BigCommerce → Shopify Increasing, esp. enterprise mid-market Developers tired of rigid templates, brands want plug-and-play apps, not custom modules.
Adobe Commerce (Magento) → Shopify High-volume exodus Cost, poor UX for non-dev teams, security overhead.
Shopify → BigCommerce Rare but happens B2B-heavy brands, unique catalog structures, multi-storefront nuance.
Headless → SaaS Quiet boomerang Marketing wants control. CFO wants predictability.

These shifts don’t come from thin air. Shopify Plus reported its highest enterprise upgrade run rate in 2024, driven by the same brands that once posted “headless” in their LinkedIn job ads. BigCommerce, for its part, has quietly cornered mid-tier B2B plays and multi-currency regional clones — where Shopify’s edges are still getting sharper but not always mature.

The Common Feature Stack

If you read enough RFPs, the wish lists rhyme. Different logos, same needs. Below is the aggregated DNA of a 2025 replatform requirement list, from SMBs to multinational wholesalers:

Feature Why It’s Non-Negotiable
B2B Portal Account-level pricing, net terms, bulk orders.
Multi-Storefront Region-specific content and currencies.
Headless APIs (selective) Keep the speed where it matters, default elsewhere.
Advanced Inventory & OMS Real-time visibility, partial shipping, backordering.
Native POS In-store and event selling — unified data.
Multi-Currency Serve global carts, local taxes.
Custom Checkout One-page flows, upsells, payment flexibility.
Subscriptions Recurring revenue bolted onto consumables.
SEO Control Clean URLs, dynamic landing pages, metadata without a dev.
Robust App Marketplace Don’t reinvent loyalty, reviews, or SMS.
Performance Hosting & CDN Fast pages, global reliability, no surprise downtimes.

Behind the Numbers: A Global View

I keep notes from these conversations: what CTOs whisper when the CFO leaves, what eCom managers actually hate about their current build, what legal flags in the SOW but never says aloud. A few truths cut across borders:

  • Brands are cost-sensitive but speed-desperate. No one wants a six-month replatform anymore. The sweet spot is 90–180 days: quick enough to swap out broken plumbing before Q4.
  • Composable is getting practical. A good operator knows which slice to make composable — custom fit engines, dynamic pricing, or an affiliate program that can’t be boxed — but the rest? They want it default, tested, and maintained on someone else’s dime.
  • No one wants to fund an R&D lab for checkout anymore. If Shopify, BigCommerce, or a specialist app has solved it, you’re wasting your margin building your own.
  • The exit door is always open. Private equity loves brands that run on clean, single-vendor tech. M&A multiples are higher when there’s no skeleton crew of legacy devs hidden behind a seven-figure stack.

A Note on the Big Losers

Not everything is upside. Adobe Commerce (Magento) is hemorrhaging mid-market share for a reason: open-source is a great badge for a CTO, but a recurring headache for marketing and finance. Similarly, custom headless builds looked brilliant when money was free. When rates climbed, burn rates became board agenda items, and the recurring developer retainer moved from hidden line item to visible cash leak.

The Smart Replatform in 2025

The best teams now treat replatforming like financial restructuring: they weigh capital efficiency, future agility, and margin control — not just feature counts. They start with a short list:

  • What’s the custom piece we can’t buy?
  • What’s a solved problem we’ll rent instead?
  • How do we make this stack portable if we need to pivot in 18 months?

Then they run hard at the migration, kill scope creep, and push live with 80% must-haves — not 100% nice-to-haves. The remaining 20%? Often irrelevant within two quarters, once the new conversion rate lands and the merchandising team can launch collections at will.

CTOs and Where We Go From Here

If you built your stack between 2018 and 2021, odds are your name was somewhere on the RFP that promised ‘true composable freedom.’ You architected it, staffed it, maintained it. And to your credit, the thing worked. It was fast, beautiful, and impressively unique when capital was patient and growth papered over burn.

A good CTO once bragged about how you built. A great CTO in 2025 brags about what you didn’t have to build — and how you reinvested that margin elsewhere.

But here’s what the past four quarters have told the market, quietly but decisively:
Marketing doesn’t want a trophy stack. They want speed. Finance doesn’t want infinite flexibility. They want predictable cash flow. The same brands that celebrated headless in 2019 are now rewriting specs for Shopify in 2025. Why? Because you can’t out-innovate an entire app marketplace with an eight-person dev squad. And you don’t want to pay the mid six-figure annual retainer for a custom build that stops A/B tests dead in procurement review.

This isn’t about abandoning architecture principles — it’s about aligning architecture with margin. Shopify didn’t ‘win’ by being the best backend. It won by lowering the cost of ‘good enough’ to near zero, and then layering an ecosystem on top that outpaces most in-house roadmaps quarter after quarter. The CFO sees that every time a dev request costs $10,000 and two sprints, while the competitor runs a plug-in on Tuesday and pivots again Friday. The marketing lead sees it every time she asks for a landing page variant and hears, “We’ll scope it next sprint.”

2025 won’t be the end of replatforms; we’ll see an acceleration of them. It’ll be the start of better ones — faster, leaner, more honest about what actually delivers ROI. As the paid social squeeze keeps tightening, a clean backend and an agile front end become margin insurance. For some, the smart play will be Shopify Plus with a composable wedge where differentiation counts. For others, BigCommerce will remain a reliable B2B tank.

And for the stubborn few, open-source will survive — but it will cost what it always did: a slice of profit to maintain what should have been standard.

Por Web Smith

Sponsored Post: D.R. es "El nuevo 321"

Editor’s Note: I’d previously and organically spoken positively about his logistics operation, going so far as to say: “Larimar Logistics offers a feasible alternative to companies seeking a strategy away from Mexico as a reliable substitute for traditional fulfillment centers with access to U.S. markets while avoiding potential risks arising from the newly imposed tariffs by Mexico.” A partner to 2PM, I have permitted their leadership to publish on this platform and I hope that it helps in your decision-making.

Larimar Logistics Is Rewiring DTC Supply Chains. If you’ve been paying attention, you’ve seen this coming.

Over the past decade, the Dominican Republic has quietly evolved into a critical bridge between global manufacturing and American commerce. Free Trade Zones have matured. Global brands have shifted production out of Asia and into Santiago and San Cristóbal. What began as a cost-saving move has become a strategic necessity, and shifting U.S. tariff policy has only accelerated this change.

Larimar Logistics was purpose-built for this moment: a single partner that combines assembly, transformation, and fulfillment under one roof, enabling brands to ship DTC with zero tariffs and same-week delivery.

Call it what it is: DR is the new 321.

The Macro Shift No Brand Can Ignore

2024 and 2025 mark the beginning of a new trade reality.

  • China is officially excluded from Section 321 de minimis eligibility.
  • Tariffs on Chinese imports can now exceed 100%, covering everything from apparel to electronics.
  • Bonded U.S. warehouses and “workarounds” are under greater scrutiny and cost.
  • Even “nearshoring” to Mexico or Canada demands upfront duty payments, complex clawbacks (IMMEX), and administrative friction.

For modern brands, this environment requires more than a freight-forwarding fix. It demands a new model.

Larimar Logistics: One Partner, Three Solutions

Larimar Logistics operates from a Free Trade Zone in Santiago, DR, paired with a U.S. fulfillment facility in Joliet, Illinois. This dual footprint empowers DTC and omnichannel brands with faster turnaround times, lower landed costs, and predictable compliance.

What sets Larimar apart is how it integrates three critical capabilities:

  • Production
    Nearshore manufacturing for garments, accessories, and hardgoods, with access to skilled, cost-effective labor. Sourcing spans global suppliers — Asia, the U.S., and Central America — consolidated to deliver a DR Certificate of Origin where possible.

  • Assembly & Transformation
    Larimar transforms goods to meet HTS shift rules, qualifying products for CAFTA-DR benefits. This legally detaches items from Chinese origin and brings the effective tariff rate to zero — not through loopholes, but through real, compliant transformation.

  • Fulfillment
    From within the DR Free Trade Zone, Larimar provides deferred-duty importation, fully 321-compliant DTC shipping, and wholesale fulfillment — without clawbacks or hidden fees. Unlike Mexico or Canada, brands avoid upfront duties and maintain full compliance confidence.

DR vs. Mexico vs. Asia: A Practical Comparison

Category Asia Mexico/Canada Larimar (DR)
Tariff Rate 46–145% ~25% 0–10%
321 Eligible No Yes (with clawbacks) Yes (no clawbacks)
Inbound Duties Paid upfront Paid upfront Deferred (FTZ)
Transit Time 30–45 days 5–12 days 3–8 days
Compliance Risk High Medium–High Low
Labor Costs Low Medium Low–Medium
Lead Times Long Medium Short

For DTC brands, these differences are not theoretical — they translate directly into better cash flow, reduced inventory risk, and a stronger margin structure.

More Than Freight: A Supply Chain Re-Architecture

Larimar is not a freight company. It is a vertically integrated, nearshore supply chain platform designed for where modern DTC is headed:

  • Faster product drops
  • Lower MOQs
  • Legal tariff mitigation
  • Direct-to-consumer compliance at scale

From blank apparel to branded headwear, from sneakers to sunglasses, Larimar enables real DR-origin manufacturing and finishing — not paper-only workarounds.

Who’s Already Leveraging This Model

Leading brands now partner with Larimar to:

  • Source materials globally and finalize production nearshore for 321-compliant fulfillment
  • Transform high-tariff categories (footwear, accessories, hardgoods) into DR COO
  • Assemble kit-based products for sports, golf, and lifestyle retail
  • Scale short-run or POD product lines with same-week shipping to U.S. customers

For brands shipping physical goods to the U.S., this is a competitive advantage in plain sight.

Control, Certainty, Compliance

Many shops operate in the DR — but Larimar uniquely integrates transformation, embellishment, inventory management, and 321 fulfillment into a single, high-compliance operation. Our capital investment, local manufacturing expertise (through D’Clase), and experienced U.S. support team help brands operate confidently in today’s shifting trade climate. Operators don’t have to:

  • Settle for fragile Asia-based 321 workarounds
  • Lock into long lead times and high MOQs
  • Trade cost for compliance

Instead, they gain a true supply chain partner that builds with their team — not around it.

Where DTC Goes Next

Tariffs aren’t going away. Section 321 will keep evolving. Consumers will only expect more, faster. Larimar Logistics is ready. Nearshore. Vertically integrated. Future-proof. For modern brands, DR is the new 321 — and Larimar is the team that makes it real.

Ready to rewire your supply chain?
[Contact the Larimar team →] Or email Scott Geftman for more information: Scott@LarimarLogistics.com

Memo: Executive Decision

It’s been a while since I have had the ability to publish on 2PM and there’s no better way to return by examining how presidential influence may reshape retail and eCommerce. After nearly three months of slowly recovering physical capacity, I am happy to be back in a rhythm.

Few presidencies have begun with such immediate and wide-ranging impacts on business strategy. Trump’s return to office has introduced an era of swift economic moves, regulatory upheaval, and intense cultural polarization—all promising significant disruption and opportunities for retailers, logistics providers, and technology firms alike. This isn’t a partisan take, but rather a pragmatic analysis of how executive power and strategic business decisions intersect.

Retailers navigating this landscape successfully will need agility in supply-chain management, proactive engagement in regulatory compliance, and strategic alignment with shifting political and consumer priorities.

The initial months of Trump’s renewed presidency have already signaled clear priorities: corporate tax reform, aggressive trade policies, and heightened scrutiny of international commerce. The anticipated revival of corporate tax cuts similar to those from 2017 is likely to provide significant financial breathing room to major retailers. Companies like Walmart, Target, and Amazon are expected to reinvest tax savings into wage increases, digital expansions, and omnichannel capabilities, reinforcing their competitive positions.

However, Trump’s renewed push on strict immigration policy and tighter labor regulations could exacerbate labor shortages, especially in retail warehousing and logistics. Rising labor costs and staffing bottlenecks may force companies to accelerate automation investments, reshaping operational strategies and potentially widening the gap between large enterprises with the resources to adapt quickly and smaller firms that may struggle to keep pace.

Perhaps the most impactful moves from the administration involve global trade. Trump’s reintroduction of broad-based tariffs targeting imports, especially from China, India, and certain European nations, has sent shockwaves through retail supply chains. Categories like apparel, consumer electronics, furniture, and home goods are again facing dramatic price fluctuations. Companies like Wayfair, IKEA, and Best Buy, heavily reliant on imported merchandise, are now under immense pressure to reconfigure sourcing away from tariff-heavy regions, diversifying toward Mexico, Vietnam, and other ASEAN countries.

Trump’s second term has intensified cultural divisions, causing brands to reassess their messaging carefully. Retailers must navigate heightened consumer activism, where brand choices have become proxies for political identity. Brands that overtly align with or against the administration risk consumer backlash or fierce loyalty. For instance, calculated enterprise brands like Nike, Patagonia, and Yeti, each known for strong value-driven identities, must delicately balance activism with business pragmatism to avoid alienating substantial customer segments.

Logistics and fulfillment have also emerged as critical battlegrounds. The administration has announced heightened enforcement of customs rules, particularly targeting the de minimis loophole previously exploited by eCommerce players like Shein and Wish for duty-free imports under $800. This crackdown, one that seems to be wavering in enforcement, would force significant adjustments among cross-border eCommerce players and prompts strategic shifts toward nearshoring and reshoring efforts.

Internationally, Trump’s presidency has begun to reshape traditional trade alliances, creating uncertainty but also opportunity. Diplomatic friction with China, ongoing tension with the EU, and renegotiations of agreements with Mexico and Canada demand retailers and suppliers to maintain agile and geographically diverse supply chains. Currency fluctuations due to geopolitical tensions will add complexity for multinational brands managing pricing and profitability.

Yet amidst disruption lie clear opportunities. Companies emphasizing American-made products could benefit significantly, as tariffs push retailers to source domestically. Technology startups are DOA without significant runaway. But defense-focused firms, like Anduril, Havoc, and Palantir may see growth opportunities as Trump prioritizes domestic security and defense spending.

Benefit or Suffer?

After some significant research, I identified 20 companies poised to either benefit or suffer significantly under Trump’s renewed presidency:

Likely to Benefit:

  • Amazon – Positioned to benefit through tax relief and robust domestic logistics infrastructure.
  • Walmart – Expected gains from reinvesting tax cuts into digital and logistics enhancements.
  • Shopify – Stands to gain as retailers pivot to independent, resilient eCommerce platforms.
  • FedEx – Increased demand from companies avoiding USPS unpredictability.
  • UPS – Benefits alongside FedEx from growing private logistics needs.
  • New Balance – Boosted by increased tariffs making domestically produced goods more attractive.
  • Tesla – Gains from pro-manufacturing incentives and robust domestic EV production.
  • Peloton – Positioned well through domestic sourcing and growing discretionary consumer spend.
  • Target – Likely to thrive through strategic investments in domestic sourcing and eCommerce.
  • Anduril Industries – Expected to benefit from increased defense budgets and border security initiatives.

Likely to Suffer:

  • Shein – Severely impacted by tightened customs regulations and tariff policies.
  • Alibaba – Faces renewed scrutiny and potential barriers in U.S. market operations.
  • Wayfair – Vulnerable to increased tariffs on imported furniture and home goods.
  • Wish – Will struggle under stricter international shipping regulations and postal rate increases.
  • Harley-Davidson – Faces international retaliatory tariffs affecting global competitiveness.
  • IKEA – Pressured by increased tariffs affecting imported European home products.
  • Overstock.com – Margin pressures due to tariff impacts on imported home décor.
  • H&M – Challenged by tariffs on apparel imports, forcing higher prices or reduced profitability.
  • Patagonia – Forced to navigate increased material import costs conflicting with sustainability commitments.
  • Allbirds – Affected by supply chain volatility, requiring strategic sourcing adjustments to mitigate tariff impacts.

Beyond policies themselves, key figures within Trump’s administration are also poised to influence the retail and eCommerce landscape.

The Acolytes

Kash Patel, Trump’s FBI Director, represents the administration’s firm “America First” approach to national security and technology. Patel has consistently voiced concerns over U.S. dependence on foreign technology, particularly from China. His previous criticism of tech leaders and scrutiny over corporate ties to foreign entities suggest future policies emphasizing stringent oversight of eCommerce platforms and data privacy. Patel’s dual stance, publicly criticizing monopolistic tech practices while previously holding interests in China-based eCommerce giant Shein, highlights potential internal complexities indicative of the greater Trump administration. Retailers should anticipate stricter enforcement of technology imports, targeted scrutiny of foreign platforms such as Shein or Temu, and possible disruptions for brands heavily reliant on China-based supply chains.

Pam Bondi, now serving as U.S. Attorney General, signals a regulatory shift toward deregulation with selective enforcement, particularly concerning corporate governance and consumer protection. Bondi’s past moves to pause enforcement of the Foreign Corrupt Practices Act (FCPA) reflect a belief that excessive corporate oversight limits American competitiveness globally. However, Bondi’s targeted criticism of corporate DEI initiatives suggests increased regulatory scrutiny of corporate social responsibility practices. Retailers might navigate fewer hurdles in international expansion but must simultaneously review internal diversity and inclusion policies to avoid potential investigations. Bondi’s immigration policies, favoring stringent labor regulations, could also exacerbate existing labor shortages in retail and logistics sectors, prompting accelerated adoption of automation technologies.

Pete Hegseth, appointed Secretary of Defense, brings a nationalist and protectionist economic ideology to the administration. Hegseth publicly supports aggressive tariffs and economic confrontation as tools for national security, notably advocating tough stances on China and even traditional U.S. allies. His backing of higher tariffs and strict export controls will likely create additional friction and cost pressures for retailers importing goods from affected regions. However, Hegseth’s advocacy for bolstering domestic production and infrastructure improvements offers potential long-term benefits for companies shifting to U.S.-based sourcing strategies. Retail brands emphasizing American-made goods or aligning with defense and patriotic themes—like Anduril Industries or veteran-founded startups—could particularly benefit from Hegseth’s policies.

Robert F. Kennedy Jr., leading the Department of Health and Human Services, injects a distinct populist and consumer-protectionist stance into the administration. Kennedy’s focus on public health and skepticism towards big corporations, especially in food and pharmaceuticals, may translate into tightened product safety regulations and increased transparency requirements in retail offerings. His early actions, including a crackdown on artificial additives and enhanced labeling initiatives, will force retailers to prioritize health-conscious product lines and rigorous compliance standards. Kennedy’s populist rhetoric against monopolistic practices also suggests potential support for antitrust actions aimed at breaking up dominant eCommerce platforms, aligning with broader bipartisan skepticism toward Big Tech.

Together, these administration figures embody the complex interplay of nationalism, deregulation, protectionism, and populist consumer advocacy.

Their combined influence suggests a retail environment marked by heightened geopolitical risk, selective regulatory enforcement, increased domestic manufacturing incentives, and growing consumer demands for transparency and safety. Retailers navigating this landscape successfully will need agility in supply-chain management, proactive engagement in regulatory compliance, and strategic alignment with shifting political and consumer priorities.

Ultimately, Trump’s presidency highlights how executive decisions reverberate through global commerce, shaping retail strategies and redefining competitive landscapes. Retailers that anticipate and adapt swiftly to these shifts—embracing agility, geographical diversification, and strategic alignment—will emerge stronger. Those that fail to respond effectively will face considerable challenges, underscoring the essential connection between political foresight and business success.

Research, Data, and Insights by Web Smith

Editor’s Note: I am returning to form after a slow recovery from a December 2024 heart incident that continues to impact me in ways that have diminished my capacity. Sorry about that, I’m good though.

Sources:

  1. Tax Policy Center
  2. The Wall Street Journal
  3. Bureau of Labor Statistics
  4. Bloomberg Retail Analysis
  5. Business Insider – Amazon and USPS Analysis
  6. CNBC Trade Coverage
  7. Federal Reserve Consumer Confidence Index
  8. Harvard Business Review
  9. New York Times Brand Coverage
  10. Retail Dive
  11. Deloitte Retail Outlook
  12. McKinsey Supply Chain Reports
  13. U.S. Customs and Border Protection
  14. Financial Times
  15. Fortune – Defense Industry Outlook