Chris Dunn, CEO at ReadyCloud, a shipping, returns and growth marketing suite built for mid-market and enterprise brands.
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Approving new technology spend is often a fairly straightforward process. It starts with a compelling proposal or a detailed demonstration. Next comes the implementation timetable, followed by the use case and the efficiency gains that integration offers.
But the most important question remains: Will the software improve company operations once it’s integrated into the day-to-day workflow? After all, complexity is ultimately the silent tax on enterprise growth.
I believe CEOs should answer that question before committing resources. A new platform can certainly improve workflow and live up to its promise. However, without clear ownership, it can also leave teams with the same obstacles and workflow disruptors the previous tech stack suffered from.
Evaluating any new technology initiative means understanding how it will improve operational scope in the short and long term. Here’s a game plan to help today’s CEOs assess this process before they open their checkbooks and sign.
1. Start with key responsibilities and ownership.
Start by understanding which employees and departments own which tasks and what obstacles are currently preventing them from delivering. A department scope overview can help assess cross-organizational boundaries and bottlenecks.
For example, consider an enterprise retailer that’s evaluating a potential new returns system integration. A product return might involve multiple departments like customer service, the fulfillment house and even finance, all of which need to coordinate before a return can be processed and a refund issued to the customer. During the software demonstration, the retailer may be shown how nimble the software is when a customer initiates a return, but the executive discussion should also explore what happens after the label is printed: who handles the customer service request, who authorizes it, how return shipping is handled and what happens if delays occur. If these responsibilities are hard to coordinate, customer service workers often end up chasing hard-to-find answers across departments.
Decision-makers should identify where these responsibilities lie, where they sit in the chain of action and which manual steps can disappear once the new tech solution is implemented. This assessment goes much deeper than simply glossing over a list of potential features a solution might offer.
2. Assess how the workflow vibes with different systems.
You already have established workflows, and connecting two different systems doesn’t always create synergy. Information may pass freely between systems, but it may get bogged down by data overload or lack the necessary context. A customer service request, for example, may come through one department with clear notes from the customer, but the customer relationship management (CRM) system may only pass on the invoice information to the next department. This can leave an informational gap that can degrade the customer experience and create added work, resulting in operational gaps that decrease efficiency and waste hours.
CEOs do not need to place every technical observation under a microscope, but they should ensure that critical workflows are tested from each end. This may involve following an order from inception to fulfillment; even a delivery exception or a refund can reveal inherent dependencies that haven’t been explored but will surface during implementation.
It’s also helpful to inquire how continuity is maintained after implementation. Does ownership end once the boundary between operational departments has been reached? Will employees have to resort to tedious manual processes, including shared spreadsheets, countless Slack messages and multiple follow-ups as the brand grows and systems become increasingly complex? Is the current system creating more work or helping streamline existing workflows?
3. Test performance under difficult scenarios.
Scalability is often discussed in terms of transaction capacity, but operational performance (and potential operational risk) involves more than processing additional orders. A business also needs to handle the exceptions, questions and decisions that accompany those orders without creating an unsustainable workload for its teams.
One of the most useful scenarios here is seasonal peaks, which are common in e-commerce. Important considerations include:
• What happens when order volume rises, delays continue, return requests spike and you also have staffing constraints?
• Will employees be able to easily identify, assess and diagnose key issues during seasonal spikes?
• Will staff be able to resolve these identified issues in a reasonable timeframe using the information that’s available to them?
• Will maintaining the new service require ongoing meetings or frequent manual interventions?
A good pilot should reflect these key operational challenges in a practical way. It should measure associated manual touches, time to resolution and even the cost per completed workflow. I advise leadership to explore these metrics to make sure the new system supports growth and doesn’t hinder it. The objective is to understand how execution changes under pressure, including whether efficiency gains survive beyond routine transactions.
4. Consider what it will take to keep adapting.
An investment should also be evaluated against the changes leadership reasonably expects. A new warehouse, fulfillment partner, sales channel or acquisition may alter how information moves and who owns particular decisions.
I’ve found that software that fits today’s operation can become expensive to maintain if each change requires extensive redevelopment. Because of this, I would examine which adjustments employees can configure, which require outside support and which depend on capabilities the vendor has yet to deliver. Data portability and integration maintenance deserve attention alongside licensing costs. Training, internal support and eventual migration also belong in the financial assessment.
Approval should define a business outcome, assign an accountable owner and set a baseline for measuring progress. Leadership can then revisit the investment after implementation to determine whether the expected improvements occurred and what needs adjustment.
The CEO’s responsibility continues beyond authorizing the purchase. By regularly reviewing whether technology helps people fulfill responsibilities, preserves continuity and supports change, the company has a stronger basis for deciding where its next investment belongs.
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