· Comparison
AI scheduling assistant vs. virtual assistant: the delegation math
AI scheduling costs $0.07–$0.21 per meeting vs. $9–$16 for a VA. Compare unit cost, scalability, and decision criteria for teams of 50–200.
SK
Sasha Krecinic
Co-Founder at SkipUp
Operations and strategy leader with experience spanning venture capital, SaaS go-to-market, and financial analytics. Previously an investor at Headline, where he co-led the firm's AI investment thesis, ran Fortune 1000 AI training programmes, and co-hosted the AI podcast. Before that, held VP-level roles at HappyCo across strategic initiatives, sales and marketing, and operations, helping scale the business through channel partnerships and customer segmentation. Now building SkipUp to give teams scheduling infrastructure that works as hard as the rest of their operational stack. Writes about the revenue operations problems he sees founders and ops leaders solve every day: coordination overhead, pipeline velocity, and the hidden cost of unmanaged scheduling.
5 articles
· Comparison
Best AI scheduling assistants for Gmail & Outlook (2026)
Compare the best AI scheduling assistants for Gmail and Outlook. No booking links, no back-and-forth — just booked meetings. See the 2026 rankings.
· Thought Leadership
Schedule meetings from an email thread — without the back-and-forth
Most meetings start as emails. Here's how to turn email threads into booked meetings without manual coordination, and why it matters for cost and scale.
· Thought Leadership
The qualification gap: AI meeting qualification starts here
Every executive has EA-grade meeting request screening. The other 95% of employees perform it alone with no tools. AI meeting qualification closes the gap.
· Thought Leadership
Scheduling is not a calendar feature. It is a revenue dependency.
The coordination tax costs mid-market companies $1,500-$4,500 per employee per year. A six-step framework for treating scheduling as revenue infrastructure.