The Art of Selling Amid an AI Boom
What door-to-door sales taught me about human skills that will become more valuable, not less, amid an AI era.
The premise
“The Art of Selling Amid an AI Boom” asks two questions: In a world where artificial intelligence has become increasingly ingrained in our everyday lives, what human traits will become more valuable, not less? And how do we use sales as a tool to leverage these traits?
The book grew out of an unlikely job I took selling window cleaning door-to-door after graduate school. Those hundreds of conversations with strangers at their doorsteps, and my move into technology sales during the AI boom, influenced my understanding of selling. Sales, whether we like it or not, is a vehicle for understanding ourselves and each other.
As AI automates workflows and becomes better at digital mass production, human-based traits will rise in scarcity, and thus in value. This book is about some of these distinctly human skills — exercising judgment, reading situations, handling rejection and uncertainty, earning trust, and making a decision to act — and how they can help us sell our ideas, projects and ourselves amid an AI revolution.
Overview
The Art of Selling Amid an AI Boom
At a time when young people are questioning their career paths and which skills will remain valuable amid AI, this offers an alternative way to think about the value of empathy and human connection from a sales perspective.
Background
Meeting hundreds of strangers at their doorsteps
The book grew out of an unlikely job selling window cleaning door-to-door in San Francisco after graduate school. Those hundreds of conversations with strangers at their doorsteps, and my move into technology sales during the AI boom, influenced my understanding of selling. Sales, whether we like it or not, is a vehicle for understanding ourselves and each other.
As AI automates workflows and becomes better at digital mass production, human-based traits will rise in scarcity, and thus in value. This book is about some of these distinctly human skills — exercising judgment; observational empathy; reading situations; handling rejection as well as uncertainty; earning trust, and making a decision to act — and how they can help us sell our ideas, projects and ourselves amid an AI era.
Reporting
Interviews, reporting and case studies
This book combines my personal narrative of selling door-to-door with case stories from businesspeople, psychologists, researchers, negotiators, as well as AI critics and advocates, to show which human skills to master amid an automated era.
Some of these door-to-door experiences include: learning to overcome more than 60 rejections before making a sale; turning an initial “not interested” into a yes; adapting the pitch to a deaf homeowner; listening to a frustrated dog owner to uncover pain points; generating a quote for a naked woman in her backyard; and sharing an Aperol sour with a couple after they bought window cleaning.
Audience
If you cringe at the idea of identifying as a “tech bro” or find it hard to market yourself, this book is for you.
According to a 2025 report from Pew Research Center, over half (52%) of U.S. workers say they’re worried about the future of AI in the workplace, and 32% think it will lead to fewer job opportunities in the future.
This book is for readers wanting to get an edge on mastering human-based skills amid an AI curve. It is for workers, creators, founders, students, job seekers, introverts, and anyone trying to sell an idea, proposal, project, or themselves — when the thought of selling can be terrifying.
There are distinctly human traits that AI, at least for now, has difficulty replacing. Mastering these skills, in tandem with learning them in an AI-driven world, will help you sell your projects, your ideas and yourself.
Selected work
Past work
Video
- DocumentaryStrangers on Our Land
BAFTA Student Award-winning and Student Emmy-nominated documentary “Strangers on Our Land” follows the killing of a Tohono O’odham man by Border Patrol, exposing a deeper history between a sovereign Indigenous nation and an entrenched U.S. federal presence. Co-directed with Zane Karram.
- Short documentaryCommunity health workers demand better pay
India relies on Accredited Social Health Activists (ASHAs), state-employed community health workers who travel door-to-door to deliver preventive care. These workers spoke with me about going on strike for better pay and benefits. Co-produced with Coral Murphy Marcos.
- Short documentaryGirls Club
A bubbly, immersive splash into the world of open-water swimming in the Bay Area, and a historic swim club that didn’t open its membership to women until the 1970s.
- The San Luis Obispo TribuneMany SLO County residents can’t find a primary care doctor. What’s causing the shortage?
San Luis Obispo County’s doctor shortage: a five-part series examining the county’s physician shortage. Photographs by David Middlecamp.
- The San Luis Obispo TribunePatients witnessed ‘erratic’ behavior from SLO doctor — one said he was sexually assaulted
Patients describe troubling encounters with a San Luis Obispo doctor, including one man who said he was sexually assaulted.
- The FriscWhat It’s Like Living in an SRO, the Cornerstone of SF’s Affordable Housing Stock
A conversation with the filmmakers behind “Home Is a Hotel,” a documentary that goes inside San Francisco’s single-room-occupancy hotels and the residents who call them home.
- Richmond PulseQuestions Remain After Richmond Officers Cleared in 2020 In-Custody Death
Prosecutors cleared the officers who restrained Jose Luis Lopez-Rodriguez before his 2020 death, but questions remain about the cause of death, a prohibited chokehold and skipped procedures. Reported with Wendy Medina and Danica Simonet.
- The FriscAs UCSF Student Workers Strike For Better Pay, Ripple Effects Hit Labs, Patients, and Life Plans
As UC student workers struck over pay in one of the world’s most expensive cities, delayed deliveries hit UCSF labs and patients, and researchers rethought their futures.
Awards
- British Academy of Film and Television Arts (BAFTA) Student Awards
Winner of Best Documentary for “Strangers on Our Land,” an investigation into the killing of Raymond Mattia, a member of the Tohono O’odham Nation, by U.S. Border Patrol outside his home in May 2023.
- California Journalism Awards
First place for health reporting and third place for best enterprise story for “San Luis Obispo County’s doctor shortage,” a five-part series in the San Luis Obispo Tribune.
- College Television Awards, Television Academy Foundation
Nominated for a College Television Award (Student Emmy) in the Nonfiction Series category for “Strangers on Our Land.”
- California Journalism Awards
Third place for health reporting for “Patients witnessed ‘erratic’ behavior from SLO doctor — one said he was sexually assaulted” in the San Luis Obispo Tribune.
Media
- The Hollywood Reporter2026 BAFTA Student Award Winners
Coverage of the 2026 BAFTA Student Awards, naming “Strangers on Our Land” the Documentary winner.
- UC Berkeley JournalismZane Karram and Kelsey Oliver’s thesis film makes Student BAFTA Awards longlist
The school’s story on the film’s path from the longlist to its Best Documentary win.
About
Kelsey Oliver
Freelance reporter, award-winning journalist and tech saleswoman
I’m a freelance reporter based in San Francisco, working in the technology industry. I’ve reported on a wide range of stories, including health care shortages in California, unanswered questions around a death attributed to “excited delirium syndrome,” community health care workers in India and the killing of a Native American man by U.S. Border Patrol.
My award-winning work has been recognized by the British Academy of Film and Television Arts (BAFTA), the College Television Awards (Student Emmys) and the California Journalism Awards.
I’m driven by an innate curiosity about the world around me. With each story comes prying. And with more prying comes deep, layered complexity. I believe it’s my job as a storyteller to synthesize these complexities with precision, truth and voice.
I’m thrilled to work on my first book, a narrative nonfiction story about door-to-door sales as a window into the value humans bring to the table amid an AI era. If you have questions or story tips about the book, please email me.
Contact
“The Art of Selling Amid an AI Boom” is an active work in progress. I’m in the depths of deep research, pitching shorter versions of the story to publications, reaching out to sources for interviews, and parsing through reporting and research around AI. So far, I’ve talked to business leaders, entrepreneurs, psychologists, writers and researchers, but there’s still a lot of reporting to be done. If you have an interesting perspective on human-driven work, AI automation or sales, I’d love to hear from you.
If you have other questions or thoughts about the book, I’m all ears.
Do you have questions about the book? Story tips? Something else? I’d love to hear from you.
Contact me