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A few months ago, I walked into the office of one of our customers, a publicly traded vertical software company with tens of thousands of small business customers. I expected to meet a traditional support team with rows of agents on the phones, sitting at computers triaging tickets. Instead, it looked more like a control room. There were specialists monitoring dashboards, tuning AI behavior, debugging API failures, and iterating on knowledge workflows. One team member who had started their career handling customer questions over chat and email (resetting passwords, explaining features, troubleshooting one-off issues, and escalating bugs) was now writing Python scripts to automate routing. Another was building quality-scoring models for the companys AI agent. This seemed markedly different from the hyperbole Id been hearing about customer support roles going away in large part due to AI. What I was seeing across our customer base looked more like a shift in how support work is defined. So I decided to take a closer look. I analyzed 21 customer support job postings across AI-native companies, high-growth startups, and enterprise SaaS. These jobs run the gamut from technical support for complex software products to more transactional, commercial support involving billing and other common issues. What I found was that customer support is being rebuilt around AI-native workflows and systems-level thinking. Yes, responding to individual tickets is still important, but roles are designing and operating the technical systems that resolve customer issues at scale. The result is a new kind of support role, one thats part operator, part technologist, part strategist. AI Skills Are Now Table Stakes For most of the last two decades, support hiring optimized for communication skills and product familiarity. But that baseline is now gone. Across the 21 job postings I analyzed, nearly three-quarters explicitly required experience with AI tools, automation platforms, or conversational AI systems. These roles are about configuring, monitoring, and improving the AI systems over time. They are reviewing conversation logs, auditing AI behavior, and identifying failure modes. In other words, AI literacy has become the baseline for modern support work. If you dont understand how AI systems behave, you cant support the customers relying on them. More than half of the roles I analyzed required candidates to debug APIs, analyze logs, write SQL queries, or script automations in Python or Bash. Many expected familiarity with cloud infrastructure, observability tools, or version control systems like Git. That would have been unthinkable in support job descriptions even five years ago. But it makes sense. When AI systems fail, they fail at scale. Diagnosing those failures requires technical fluency like understanding how models interact with external systems and when an issue is rooted in configuration versus product logic. The job has evolved from fixing problems ticket by ticket to preventing the next thousand tickets. Humans are Needed to Solve Harder Problems Once AI becomes part of the support workflow, the nature of the work becomes more technical. One support leader I spoke with at a company that now contains more than 80% of its tickets with AI put it plainly: once automation handles the easy questions, the work left behind gets harder. The same frontline agents who used to focus on quick wins are now handling the most frustrated customers and edge cases, and theyve had to scale up their skills accordingly. In practice, this often looks like a customer trying to complete a critical workflow, like syncing data between systems before running billing. An AI agent starts by working off documentation that a subject matter expert has synthesized from multiple functions across the company. From there, the AI agent can confirm that everything is configured correctly. However, the AI agent may not be integrated to the right underlying system that failed silently hours earlier. The customer follows the guidance, only to discover downstream that data didnt move as expected. When the issue escalates, the subject matter expert has to reconstruct what happened across systems, reason through what the AI agent missed, and help the customer recover without losing trust. This is the kind of end-to-end work that AI still cant do on its own. It requires both technical fluency to trace failures across disparate systems, in addition to human judgement to decide what can be fixed immediately versus what needs deeper product or engineering intervention. In this way, support has become less about answering questions out of the manual, and more about creating the manual and solving the problems that it doesnt cover. The Hybrid HumanAI Model Is the Default Despite widespread fear about AI replacing support jobs, not a single posting I analyzed suggested that support would be 100% automated in the future. Instead, nearly every role gravitated toward a hybrid model where AI handles routine interactions, while humans oversee quality and continuously improve the system. This makes sense when you consider the fact that 95% of customer support leaders said they would retain human agents in their operations to help define AIs role when surveyed by Gartner last year. Titles like AI Support Specialist, AI Quality Analyst, and Support Operations Specialist were almost entirely focused on orchestration, designing escalation logic and defining when humans step in. This is where the earlier control room image becomes reality. The work of humans changes from simply answering questions to actually shaping systems. Taken together, these trends point to a single conclusion: customer support is specializing. The repetitive work is going away, but the judgment-heavy, technical work is expanding. That shift is already visible in how companies hire. The question now becomes whether organizations (and workers) are ready to adapt fast enough.
Category:
E-Commerce
Forget about the big game on Sunday. Two heavyweights have been battling it out this week over a topic thats become all-too-familiar over the years: advertising creep. Its a tale as old as time, in some respects. Many a CEO have proudly declared that their companys platform or services will remain ad-free, only to later succumb to the lure of all that advertising revenue and embrace it. And thats creating a new divide among AI platformsone that will play out to the worlds largest TV viewing audience during the Super Bowl. Among the nearly dozen AI-related ads on Sunday will be two 60-second spots each for OpenAI and Anthropic. While OpenAI will use its time to tout how its ChatGPT helps people build things with a real-world impact, Anthropic is taking a swipe at its much-larger competitors recent decision to incorporate ads into the platformand its virtuous decision to keep its Claude AI assistant ad-free. This off-field action has already made for some entertaining viewing. Anthropic dropped four ads this past week set to Dr. Dres 2001 song Whats the Difference, which all conclude with the same warning: Ads are coming to AI. But not Claude. That elicited a lengthy post on X by Sam Altman, OpenAIs CEO, thats since become the topic of much ridicule. While Anthropics Black Mirror-esque ads are extremely clever, theyre also strategic, as the company seeks to position itself much like Apple has with its privacy-first messaging, says John Battelle, an entrepreneur and author. Claudes marketshare may be a tiny fraction of ChatGPTs, but Anthropics swipe at OpenAIs reversal on advertising was well-playedand it makes an important point, according to Battelle. I applaud what they did,” he tells Fast Company. “This needs to be talked about.” Pivot to revenue For Altman, the advertising U-turn took about 15 months. In October 2024, he said that he viewed advertising as a last resort as a business model for OpenAI, only to seemingly reverse course a few weeks ago. Hes hardly the first to do soand for good reason. Theres no question that the only business model that you can employ if you want to scale a business is advertising, Battelle says. Advertising . . . finds a way Recent decades have seen a well-trod path for companies that transitioned to an advertising-supported business model from one that was originally based on subscriptions or, seemingly, free for users. Advertising has slowlyand sometimes not so slowlycrept into almost every major platform controlled by a large tech company, whether it’s social networks like Facebook or streaming services like Netflix, to name a few. But Google perhaps offers the canonical example of a companys founders finding their advertising religion and walking back prior vows to remain ad-free, says Battelle, whose book The Search: How Google and Its Rivals Rewrote the Rules of Business and Transformed Our Culture” was published 20 years ago by Penguin In a 1998 white paper laying out their vision for Google, cofounders Sergey Brin and Larry Page didnt mince words about the potential mixed incentives of a commercial search engine with a business model predicated on advertising. The goals of the advertising business model do not always correspond to providing quality search to users, wrote the duo, then-PhD students at Stanford University. We expect that advertising funded search engines will be inherently biased towards the advertisers and away from the needs of the consumers. In 2000, Google began selling advertisements. To say it’s become a big business would be an understatement. Parent company Alphabet reported this past week that Google advertising accounted for more than 72% of its $113.8 billion revenue in the fourth quarter. A hill to die on For some founders, advertising has been a hill theyve been willing to die on. Clashes about advertising on WhatsApp were reportedly among a variety of reasons why cofounder Jan Koum ultimately left parent company Facebook (now Meta Platforms) in 2018, four years after the messaging app was acquired. Koum had long expressed his disdain for advertising and how it worsened a product. He vowed to keep advertising out of an app where people communicate with friends and family, and his first-ever tweet was a quote from the movie Fight Club that pulls no punches: Advertising has us chasing cars and clothes, working jobs we hate so we can buy shit we dont need. Last year, WhatsApp debuted ads in the app. The future of advertising on AI Like many before them, the founders of AI companies must now determine where their line in the sand is on advertising. And its no surprise that advertising has eventually found its way into AI platforms, as Battelle laid out in a recent blog post. As Google, Facebook, Uber, and other companies have taught us, advertising creep does gradually change the services we know and love, Battelle says. In some cases, like with Instagram, the product today barely resembles its pre-advertising self. When you commit to advertising, you commit to the incentives of advertising, he says. Even if advertising on AI platforms will inevitably evolve with time, Battelle says an imperative question now is what that future will look likeand particularly if social media is the reference point. Man, things are not going to be pretty if the business model that drove social media also drives generative AI.
Category:
E-Commerce
Taking the leap from traditional employee to solopreneur involves a number of decisions and considerations that may come as a surprise if youve always been on someone elses payroll. Being numero uno for every part of your solo enterprise can illuminate just how complicated it can be to keep any kind of business running. Unfortunately, becoming a solopreneur can complicate your personal financial choices as well. Thats because money habits that felt innocuous while you were on a biweekly pay schedule can create financial mayhem on an irregular income. Whether youre considering becoming a solopreneur or have been rocking the solo business world for a while, make sure you dont carry these common paycheck habits with you into your entrepreneurial venture. Ignoring your bank balance Prior to becoming a teacher, I worked a series of low-paying jobs, including several stints where I stitched together multiple part-time positions. During that period of what we might generously describe as my early career, it was my habit to check my bank balance daily. This was in the early 2000s, when the internet still required a kerosene-powered modem to access Google, so it took some effort on my part to indulge in this habit. But since I was making so little money, I needed to know on an almost daily basis what was happening in my account to make sure I hadnt overlooked anything. When I started teaching and bringing in the medium bucks, it was a relief to only check my bank balance when I paid my bills rather than every single day. As a public school teacher, I knew exactly how much money I received in each paycheck, I knew exactly when it would clear my account, and I knew that if my mental accounting was off by a little bit, I didnt have to wait long for the next paycheck. (Ironically, the only time Ive ever overdrawn my account was during the regular-paycheck years of my life.) Befriend your banking tools Becoming a solopreneur is a little like going back to your early twentysomething career, at least financially. Keeping a weather eye on your finances is the only way to stay ahead of problems before they blow up. Theres no steady paycheck to smooth over any issues. The good news is that banking technology has come a long way since I had to keep my modems kerosene tank full just to log onto the internet. These days, virtually every bank and credit union under the sun has an app that will allow you to set up personalized alerts and text notifications, among other tools. This makes it very easy to set up regular bank balance check-ins, whether you create an alert to notify you when your balance dips below a certain dollar amount, or you have your bank text you the current balance every day at the same time. Waiting for tax season Paying taxes is no ones idea of a good timebut at least when youre working for a paycheck, the taxman knocks but once a year. Whether you use a CPA or do them yourself, taxes are fairly straightforward for those who are traditionally employed. Once you have your W-2 in your hot little hand, you can typically get started sometime in early spring, then patiently wait for your tax refund to arrive . . . and youre done until next year. But solopreneurs dont get the luxury of treating taxes like a sucky annual holiday. Because small-business owners dont have taxes withheld from their income, they have to pay quarterly estimated taxes, filing each payment with Form 1040-ES. The approximate due dates for each payment are as follows, but they may be pushed back if the 15th falls on a weekend or holiday. First quarter (January 1-March 31) Due April 15 Second quarter (April 1-May 31) Due June 15 (June 16 in 2026) Third quarter (June 1-August 31) Due September 15 Fourth quarter (September 1-December 31) Due January 15 Solo business owners also typically have to deal with much more complicated tax reporting if they have multiple clients. That means they are fielding more tax formssuch as 1099-NEC and 1099-K formsthan traditional employees. Build tax infrastructure into your business Paying and organizing solo business taxes are overwhelming if you only think about them when theres a due date. But they can be an easy part of your daily routine if you build tax infrastructure into your business plan. For quarterly estimated taxes, it starts with planning ahead for paying Uncle Sam. You can do that by creating a savings account where you transfer about 20% of each payment you receive. This will ensure that you always have the money you need to pay your estimated taxes each quarter, so youre not scrambling to find the cash every three months. Over time, you can adjust how much you set aside for taxes as needed. As for organizing your taxes, this can also be a relatively simple and ongoing part of how you conduct your business. Its important for solopreneurs to have an accurate account of their income, since its always possible a client will make a mistake on the 1099 they issue. An invoicing structure where you record income from specific clients at the same time you mark their invoices as paid can be a small tweak that will make tax organization much easier. This could be as simple as a Google sheet that you keep updated, as long as you are consistent. Taking no vacation days When you work a traditional job, it can be easy to forget to take time off. Whether you get a set number of vacation days per year, or your workplace offers unlimited PTO (which really means you get the hairy eyeball if you try to schedule any), its easy to reach the end of December before youve realized you never took a vacation. This is obviously a serious problem within the American workforce, which is suffering from burnout, lack of work boundaries, and a bad case of the Mondays. While none of that is good, many workplaces do at least offer regular time off in the form of weekends and federal holidays. Workers who habitually leave their vacation days unused can still count on several long weekends and other breaks throughout the year to give them a needed opportunity to rest. Block off time for rest Working for yourself means you dont have to stick to a 9-to-5 schedule, but it also means you might be working at midnight, on weekends, and through Thanksgiving dinner. The habit of working without a vacation can be especially tempting when your success or failure depends on your hustle. But youre solely responsible for your business now, which includes the well-being of your only employee. You cant rely on the holiday calendar to provide you with time away from your work like you did as a paycheck employee. You have to set the boundariesor deal with the consequences of burnout. Which could mean not being able to work at all. This is why you need to set the boundaries your previous schedule gave you automatically. You can do this by blocking off time weekly, monthly, and annually for rest. If you need to, imagine that your rest times are legally mandated so that youre not tempted to work through your vacation time anyway. Building better habits Working for yourself, by yourself, doesnt just require a change in how you structure your work dayyou may also have to revamp your personal financial habits. Without the safety net of a steady paycheck, solopreneurs cant afford to ignore their bank balances like they did as an employee. Your banks mobile app and online tools can help you keep track of your finances with automated alerts and notifications. While paycheck employees get to think of taxes as a single season of the year, solopreneurs have to deal with tax chores year-round. That includes paying quarterly taxes and keeping records organized. Setting aside around 20% of each payment can help solo entrepreneurs have the money they need to pay their estimated taxes every quarter, while recording their income as the invoices are paid can help make tax reporting easier come April. And though all Americans need to take more time off, those working traditional jobs can often count on weekends and federal holidays, even if they forget to use their PTO. Solopreneurs can get stuck in an endless working cycle unless they specifically block off regular time for restand guard it fiercely.
Category:
E-Commerce
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