Alysha Daytner Took the Scenic Route to the CMO’s Office

Alysha Daytner’s résumé contains a small rebellion against the straight line. It begins with communication, passes through mobile software and six years of education nonprofit operations, turns toward advocacy, loops around the Chicago Marathon and arrives in the marketing organization of a public software company. Read only the job titles and it seems like a sequence of pivots. Read the work underneath and the route becomes clearer: she has spent her career helping complicated groups of people move in the same direction.

Today, Daytner is Chief of Staff to the CMO at Sprout Social. Inside the company she is known as “AD,” a practical solution to an office already occupied by an Alicia. The nickname suits the economy of her public voice. She writes in crisp lists, thanks collaborators by name and makes room for the comic detail. A job opening in Chicago comes with “keys to the swag closet.” Another comes with a promise to reveal where the snacks live.

The humor matters because the work can sound bloodless from a distance. Business operations. Cross-functional alignment. Executive support. These are phrases designed to survive a spreadsheet. Daytner’s version is more human: who needs context, who should be in the room, what does the audience want, and how early can everyone begin?

01 · The first long tripA communications degree, then Beijing

Daytner graduated from Purdue University in 2008 with a degree in communication. That summer, she joined a Purdue group sent to Beijing to help with media work connected to the Olympic Games. It was an unusually large stage for a new graduate and an early lesson in coordination: unfamiliar customs, global visitors, fixed deadlines and no useful way to ask the opening ceremony for an extension.

Her first professional chapter was marketing and public relations at Open Kernel Labs, a mobile virtualization software company. Then, in 2010, she entered Teach For America as an operations assistant. Over the next six years she moved through strategy, operations, leadership development, team operations and special projects. The titles changed because the scope did. By the end, she was directing special projects after years spent learning how an organization works from several angles.

At Educators for Excellence, she first carried the Chief of Staff title. Her recommendation from a former Teach For America colleague points to the kind of operator she had become: able to manage detail, work across difference and deliver under pressure. Then came a literal course change. In 2018, at Chicago Event Management, her remit included partner relations and logistics tied to the Bank of America Chicago Marathon.

There is an appealing symmetry here. Years later, Daytner would use racing to explain her working life. She is an ultrarunner herself, with public results at two 50-kilometer events and the 2024 JFK 50 Mile. The sport makes patience measurable. A runner can have ambition at breakfast and still has to cover every mile.

02 · Entering software sidewaysThe useful risk of starting over

Sprout Social first lodged in Daytner’s mind in 2016, when she encountered the company on a list of good Chicago workplaces. B2B software was absent from her plan. Sprout kept resurfacing anyway. In 2019 she joined as Manager of Events, trading senior nonprofit titles for the chance to learn a new business.

She later described the decision plainly: changing industries meant hitting reset on title and level. It was a risk, but she had not arrived empty-handed. She brought the resourcefulness of nonprofit teams, years of operating experience and a willingness to ask questions without pretending to know the answers. “I still Google things I don’t know (this is allowed!),” she wrote after a later promotion. The parenthesis is doing excellent work. It turns uncertainty from a confession into a habit.

The leap is the first reward, but there are plenty more to follow.Alysha Daytner on nonlinear careers

The progression at Sprout came in distinct stages. After events, she became Senior Business Operations Manager for marketing in 2022, Business Operations Director in 2023 and Chief of Staff to the CMO in 2024. She has since announced a promotion to Senior Director while keeping the same Chief of Staff remit and continuing to work with CMO Scott Morris.

A friend gave Daytner the most useful framing for the journey: her network now spans two categories of expertise. That is the dividend of the reset. A conventional ladder might have produced a higher title sooner. Her detour produced bilingual judgment, the ability to recognize patterns shared by mission-driven nonprofits and a growing software business while respecting the differences between them.

03 · No wand requiredThe operating philosophy hidden inside an event

In 2021, Daytner published a conversation with Sprout colleague Rachael Samuels about how event and social teams work together. The piece begins with a familiar corporate request: “work your magic.” Daytner dismantles the phrase with affectionate precision. Behind a successful event sit strategy, data and user experience. The sparkle arrives at the end; the shared documents arrive first.

Her advice is practical. Define the audience. Use social listening to test assumptions about what that audience wants. Decide whether the moment calls for a keynote or a workshop. Bring social teammates into planning early. Put them in the run-of-show. Share deadlines for images and quotations. Explain what happens to their work when materials arrive late.

The philosophy scales neatly from a single event to the CMO’s office. A chief of staff lives at the intersection of good intentions and finite attention. The role asks for translation between functions, sequencing across priorities and enough trust to say when a plan needs to slow down. Daytner’s career has been an extended apprenticeship in precisely those conditions.

She also knows that people remember how a system feels. Her old Sprout biography lists three unofficial specialties: candy connoisseurship, book recommendations and Facebook Marketplace counsel. Those details sit comfortably beside event strategy because hospitality and operations are cousins. Both begin by noticing what another person might need before they have to ask.

04 · Training days, racing daysDiscomfort with a finish line

On her sixth anniversary at Sprout, Daytner compared the company’s earlier years to a Turkey Trot. The young business was growing, office-centered and relatively comfortable. The newer version felt like racing: hungrier, less comfortable, more willing to fail, adjust and try again. She admitted that training is her favorite part and race day is not.

Then came the operator’s correction: “Training without racing is just maintenance.” Preparation needs a test. Private effort eventually requires a launch, a decision or a public promise with consequences. Her own route supplies the evidence. She trained across organizations and disciplines, then repeatedly chose the line: a new sector, a larger remit, an ultradistance start.

That willingness now sits inside a company navigating another period of change. Sprout has expanded from social publishing and engagement into listening, influencer marketing and AI-powered intelligence. Daytner publicly welcomed the NewsWhip team after Sprout acquired the predictive media-intelligence company in July 2025. Her response focused on what the combined teams could help businesses do, a small example of the connective work expected from the CMO’s office.

Her commitments outside the immediate job add another loop to the story. In 2025 she became executive sponsor of Sprout’s Underrepresented Genders in Tech employee group. That October, she began coaching with One Million Degrees, an organization helping Chicago-area community college students navigate education and careers. After moving from education into software, she found a way to keep a hand in both.

Training without racing is just maintenance.Alysha Daytner

Daytner’s career makes a quiet argument against mistaking novelty for reinvention. She did not become a different person each time the industry label changed. She carried forward a set of verbs: organize, listen, translate, anticipate, convene. The marathon course and the marketing organization both reward someone who can see the handoffs.

There may be no single correct route to a CMO’s office, which is fortunate because the scenic one has better stories. It can pass through a Beijing media center, an education nonprofit, a race-day operation and an events team. It can include a lower title, an unfamiliar acronym and a search box open for the things you have not learned yet. It can even pause at the snack cupboard.

The point is to keep moving with enough attention to notice what the detour is teaching. Daytner’s race results contain elapsed time, distance and rank. Her professional record contains a subtler measure: each chapter enlarged the number of rooms she knows how to help run. For an operator, that may be the distance that matters.