Business
The Startup Hiring Mistake That Looks Like a Win
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Published 10/12/2026 1:30:00 PM
The Startup Hiring Mistake That Looks Like a Win
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Key Takeaways
- Many founders make the mistake of hiring a senior leader before the infrastructure exists to support it. They expect the leader to produce results off of a strategy that doesn’t exist yet.
- Read the signs before you hire: no repeatable way leads or customers come in, the budget depends on whoever’s cheapest rather than what’s working, no one knows which channel actually drives revenue.
- Set them up before day one: They need clear business goals, real decision-making authority, access to data and alignment with the founder on priorities.
- Consider fractional leadership: Real work gets done, and you learn what the role actually requires before you commit to a salary and a title.
In July, WHOOP hired Dirk-Jan van Hameren, Nike’s former chief marketing officer, to run marketing for the wearable-tech company. On paper, it looked like a typical senior marketing hire. In practice, van Hameren walked into a company that had just closed a $575 million funding round at a $10.1 billion valuation, crossed 3 million members and was already cash-flow positive.
He didn’t build a marketing function. He inherited one: a 65-person team already in place, reporting directly to him from day one.
That’s the part founders miss when they look at a hire like this and think, “We’re ready for that, too.” I’ve spent years placing marketing talent inside growth-stage companies, and the mistake I see most often is making a senior hire before the infrastructure exists to support it.
Here’s how to tell whether your company is actually ready to hire a marketing VP or CMO, and what to do if it isn’t yet:
1. Read the signs before you hire
These signs usually mean the infrastructure isn’t there yet for a VP or CMO, even if the ambition is: There’s no repeatable way leads or customers come in yet, the marketing budget depends on whoever’s cheapest that quarter rather than what’s working, and no one on the team could tell you which channel actually drives revenue.
I worked with one founder who got excited about a strong résumé, made the hire and then wondered, six months in, why nothing had changed. The new leader was spending most of their time on hands-on execution instead of building a team or a strategy, while the rest of the leadership team kept expecting immediate growth results. That expectation was the real problem.
A senior marketing leader‘s first few months should go toward diagnosing what’s actually working, not producing results off a strategy that doesn’t exist yet. Skip that step, and any growth you do see won’t hold. In most cases like these, the company would have been better served by a strong director-level marketing leader first, then an executive once the complexity and scale actually justified the title.
A director-level hire costs less, comes with lower expectations attached and is often more comfortable doing the hands-on work the company actually needs right now. That’s the hire that fits what the company can currently support — nothing about it is a step down.
2. Set them up before day one
A senior marketing leader needs four things in the first 90 days: clear business goals, real decision-making authority, access to data and alignment with the founder on priorities. They also need context, including what’s been tried before, what’s working now and where the company wants to go. Without it, a new hire will spend their first month rediscovering things the company already learned the hard way, such as channels that never converted or messaging that fell flat with the sales team.
Founders fall short here constantly, changing priorities every few weeks, withholding real authority while still expecting ownership or demanding results before the leader has had time to build a strategy grounded in the company’s actual data. A 2025 Gartner survey of CEOs and CFOs found only 34% see eye-to-eye with their CMO on marketing’s role in supporting growth, which is exactly the kind of misalignment that turns a strong hire into a six-month disappointment.
3. Close the gap without the full-time price tag
Fractional leadership exists to help close this gap. It makes sense when a company needs senior-level strategy and expertise but isn’t ready for the cost, scope or workload of a full-time executive — particularly during periods of growth or transition, or when the marketing function itself still needs to be built before anyone commits to a permanent leader.
Alina Vandenberghe, co-founder and co-CEO of Chili Piper, used this approach after running marketing herself for a stretch, hitting her numbers but exhausting the model. Rather than hiring a full-time CMO right away, she brought on a fractional marketing executive to test what skills and attributes her permanent hire actually needed. A short, defined engagement (three to six months, with specific goals attached) gives you the same clarity.
Real work gets done, and you learn what the role requires before you commit to a salary and a title. Vandenberghe landed on a full-time VP of marketing once that was clear. Van Hameren’s move to WHOOP shows the other end of that same process. The team, the budget and the scale were already there waiting for him, which is precisely why a full-time hire made sense.
Before you hire the VP or the CMO, ask whether your company looks anything like that. If it doesn’t yet, that’s not a reason to wait indefinitely. It is a reason to build the infrastructure first, so that when you do make the hire, you’re not asking someone to do a job you were never set up to give them.
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Effective product pages help online shoppers decide whether an item fits their needs and what buying it involves. A beautiful photograph gets attention. Product details such as dimensions, available sizes, delivery details, and a clear price help turn that attention into a purchase.
Even established retailers miss these basics. In its benchmark of leading U.S. and European retailers, updated in March 2026, Baymard Institute rated 52% of desktop sites and 62% of mobile sites “mediocre or worse” for product-page usability1.
Product-page changes can affect revenue, too. In a 27-day test for Life Pro Fitness, agency Media Contour made product images, key details, and buying buttons visible without needing to scroll. Testing vendor Wingify reported that the revised page generated $0.67 more revenue per visitor than the original2.
If you are building a new store, follow the five tips below as you create your product pages. Have those pages ready before running ads that send shoppers to them.
If you already have an online store, choose one product page to improve. Reference these steps to check whether it answers shoppers’ questions and lets them add the right item to their cart.
1. Answer shoppers’ questions in the product description
Identify the main question a shopper needs answered before buying. Look for questions customers ask repeatedly or misunderstandings behind returns. For a new product, start with fit, compatibility, or what is included. Confirm the answer against your product specifications, then put it near the start of the description.
For example, consider a pet-supply retailer selling a dog harness. Someone choosing their first harness needs measurements and adjustment details to judge the fit. Someone replacing a harness they already own needs to recognize the same model and size. The page should make both tasks straightforward.
Also, use consistent labels and units across similar products to make comparisons easier. Include limitations, such as incompatible models or items sold separately, so shoppers can rule out an unsuitable purchase.
In e-commerce platform BigCommerce, for instance, online sellers can use the product description and custom fields—additional facts such as material or compatibility—to present these details. Preview the product page to check that shoppers can find the information they need.
Then, use those same facts to help shoppers recognize the item in search results. In BigCommerce’s page title field, use the product name and a relevant detail, such as its model or material. Avoid repeating keywords or giving every product the same title.
2. Give every product image a question to answer
Plan your gallery around what someone needs to inspect. Show the whole product, a useful detail, and the product in use. For example, a lighting retailer could photograph a lamp beside a chair to show its scale and how it lights a reading space. A close-up of the switch shows how someone would operate it. Together, these images help shoppers picture using the lamp at home. Keep written dimensions available as well.
The same Baymard overview describes how shoppers use images to judge size and can struggle when photographs lack a familiar reference.
If you sell a bundle, make clear which pictured items are included. For products that need assembly or demonstration, you might even consider creating a short video. Add alt text: a short description of the useful information in an image. Screen-reader software can read that description aloud or present it in braille. Keep essential instructions available as text as well.
BigCommerce supports product images, images for variants such as different colors, and YouTube-hosted product videos. Check that your gallery presents the right item as shoppers change their selection.
3. Make choices, prices, and recurring charges clear
Keep size, color, quantity, and purchase options close to the buying button. Label them plainly, show the current selection, and make unavailable choices recognizable. If the size options fit on the screen, show them as labeled buttons, such as S, M, and L. This lets shoppers see which sizes are available without opening a menu, as the Baymard overview explains.
Place helpful links beside the choice it explains. For the dog harness, for example, consider putting a measurement guide beside the size selector so shoppers can check the fit before choosing. Keep it visible or provide a clearly labeled link that works by touch and keyboard.
In BigCommerce, online sellers can configure choices such as size and color through product variants and options. Then check that the displayed price and availability match the shopper’s selection. For multipacks, show both the pack total and the unit price. Make the full pack price easy to find so shoppers know what they will be charged.
If you offer subscriptions, let shoppers explicitly choose between a one-time purchase and a recurring order. Put the recurring charge, delivery frequency, and change or cancellation terms beside that choice so shoppers can compare the commitments before selecting. Confirm that these terms match how your subscription service works. Select a subscription yourself and verify that checkout shows the plan, price, and frequency you chose.
4. Make sure delivery, returns, and reviews are easy to find
A shopper who needs an item by a particular date wants to know whether it will arrive in time. Show a delivery estimate for their destination. Put a short explanation of shipping and returns near add to cart, with links to the full policies.
Show shipping fees or explain how they will be calculated. Clearly describe return windows, fees, and exclusions that matter for the item. If pickup is offered, distinguish stock at the selected location from stock elsewhere. Avoid presenting an estimate as a confirmed promise.
Also consider making reassurances that are specific to the purchase. Using the dog harness as an example again, you’d want to explain whether a shopper can exchange it if the fit is wrong and which conditions apply. That answers the practical concerns that a badge saying “Shop with Confidence” leaves unresolved. Use only promises your business can honor.
Customer reviews provide another way to assess the product. Show the review rating, text, reviewer’s display name, and date on the relevant product page. If reviews come from another service, name that service. These details help shoppers understand whose experience they are reading and how recent it is.
5. Test the path from product page to cart
Shoppers need to know that the page has registered their choices and whether adding an item succeeded. Open your chosen product page on your phone. If a required option starts unselected, try adding the item before choosing it. The page should tell you what to select or explain why “Add to cart” is unavailable.
If the product has options, choose them, then change one selection. Check that the price, availability, and any option-specific images match. Add the item. While the request is processing, the page should make that clear. Once it succeeds, a confirmation or the cart itself should show what was added. If an error occurs, it should explain how to continue without losing other selections.
From there, make sure to check the item’s quantity, options, and price in the cart. If you chose a size or color, return to the product page and check whether it still shows that selection. These checks help catch a wrong selection or an uncertain result before a shopper encounters it.
Shoppers who cannot use a mouse need to select options and add products using a keyboard. To check that they can, repeat the steps above on a computer without the mouse. Use Tab to move forward between controls and Shift+Tab to move back. A visible outline or other marker should show which control you are about to use. Press Enter to activate links and Enter or Space for buttons. In a drop-down list, such as a size selector, use the arrow keys to move through the options.
Shoppers who need larger text must still be able to read product details and reach Add to cart. Use the browser’s Zoom control to enlarge the page to 200% and try the same steps again. Check for overlapping text or controls that disappear. Across all these checks, record anything that prevents choosing the product, adding it, or correcting a mistake.
Keep improving one page at a time
Clear facts and images help shoppers judge the product; clear choices, terms, and working controls help them act on that decision. Choose one issue from your review to fix first. Give priority to a problem that prevents adding the correct item to the cart. If shoppers can add the correct item, address an unanswered question that could lead someone to buy the wrong product.
Record what you changed and when. If you have sales reports, compare purchases and revenue for the product over equal periods before and after the change. Note any promotions or changes in visitor numbers that could also explain the results. Customer questions, order corrections, and return reasons can help you check whether the same misunderstanding persists.
For more examples, explore BigCommerce’s product-page guide, then apply the same review to the next product page.
1 Product Page UX 2026: 10 Pitfalls and Best Practices (Baymard Institute)
2 Media Contour uses split URL testing to improve the revenue from product pages (Wingify)
