At a glance
- Who: Shawn Dej, co-founder and CEO of YourStory AI
- Company: a teacher-controlled AI learning platform used in 230+ institutions
- Team in Dock: 8 agents, led by his chief of staff, Cass
- Roles covered: SDR, inbound email, active users, trial to paid, RFP and procurement scanning, conferences, investor outreach
- So far: 550+ education contacts tracked, 40-50 personal emails and 20-30 follow-ups on a busy day, replies in minutes instead of hours
YourStory AI builds what it calls the first fully teacher-controlled AI assistant: students talk with historical figures and science characters, and teachers shape every lesson and review every conversation. It's used in more than 230 institutions, from Oklahoma City Public Schools to Sausalito Marin City School District (useyourstory.ai).
Shawn Dej is the co-founder and CEO, and he runs outreach himself. Selling to schools runs on relationships with teachers, principals and districts, with RFPs and procurement rules on top. Before Dock, his outreach, follow-ups, tracking and inbox triage all lived in his own inbox and spreadsheets. "Things slipped and I was the bottleneck."
The sales org
Shawn built an eight-agent sales org in Dock, and nothing is sent until he approves it.
- Cass, his chief of staff, has the day's brief ready each morning, sends three roundups through the day, keeps every follow-up on schedule and drafts everything for his sign-off.
- An SDR works 400+ schools and 150+ community colleges, each one tracked.
- Specialists scan RFPs and procurement notices, plan conferences, handle inbound email, watch active users, move trials to paid and run investor outreach, all without being asked.
Because he can text Cass, approvals happen from his phone in the evening or between meetings. "That one's a big deal for me."
Illustration of Shawn's setup. The district name and counts in the conversation are examples.
A day with the sales org
- Morning: Cass has the brief ready: replies that came in, follow-ups due, and anything new from the RFP and procurement scan.
- Through the day: three roundups keep Shawn current. The SDR drafts personal outreach to schools and community colleges, and every draft waits in a queue for his OK.
- Evening or on the go: Shawn approves by text. Approved emails go out, and the follow-up cadence picks up from there.
- In the background: the other agents watch active users, move trials to paid, plan for upcoming conferences and keep investor outreach moving.
What Shawn still decides
Nothing reaches a school, district or investor without Shawn's approval. He decides who to pursue and what gets said. The agents do the research, drafting, tracking and follow-up that used to pile up in his inbox.
What it adds up to
- 550+ education contacts in an active, tracked pipeline
- 40-50 personal outreach emails and 20-30 follow-ups on a busy day, every one approved by Shawn
- replies in minutes instead of hours
"Dock is a must have for entrepreneurs. Pure gold."
Small teams, big companies: read why.