Winn.ai raises $18M Series A for a real-time AI sales assistant
Winn.ai has closed an $18 million Series A to scale its real-time AI assistant for sales teams. The tool sits in the call, prompts reps in the moment, and handles the before-and-after admin that drags deals and burnouts pipelines.
Insight Partners, S Capital, and Mangusta Capital co-led the round, with participation from Moneta VC, HighSage Ventures, Alumni Ventures, Sarona Ventures, and OurCrowd. The Tel Aviv-based company, founded in 2022 by CEO Eldad Postan-Koren and CTO Bar Haleva, has now raised $35 million to date.
Funding for AI across sales and marketing neared $4 billion last year, per Crunchbase data-higher than 2024's $3.4 billion, though still below 2021's peak. The signal is clear: buyers are moving from "nice-to-have analytics" to tools that help reps execute during the call.
What Winn.ai actually does for reps
- Live guidance during prospect and customer calls so reps ask the right questions at the right time.
- Automates pre-call prep and post-call work-action items, summaries, and CRM updates.
- Integrates with enterprise CRM and business intelligence systems to keep data clean and usable.
Postan-Koren frames the category gap simply: most tools analyze recordings after a deal slips. Winn.ai focuses on the moment it matters-the live conversation-so coaching turns into execution, not a retro post-mortem.
Execution over analytics
Conversation intelligence has given leaders more dashboards. The problem is the lag-feedback lands a week later and gets ignored in the rush of quarter-end. Winn.ai flips that by guiding reps on what to do right now, while still capturing the data leaders need.
Traction, customers, and what's next
The company says it tripled ARR in 2025 and delivered 30x growth over the past two years. It serves dozens of customers, including Deel, Kaseya, and Cyera, on a standard per-seat SaaS model. Winn.ai isn't profitable yet.
New capital will grow the U.S. go-to-market team and continue heavy R&D investment. The primary market is the U.S., with growing organic traction in the U.K. and Europe. While the product started with account executives, demand has expanded to SDRs, account managers, solutions engineers, and customer success-plus early interest from support and HR teams.
Investors say the appeal is consistency at scale. The assistant helps leaders drive playbook adoption across every rep and bring teams closer to predictable execution, not just more reports.
If you lead a sales team, start here
- Run a 60-90 day pilot with two squads (one outbound, one mid-market/AE). Keep a clean control group.
- Define non-negotiable metrics upfront: win rate, cycle time, stage conversion, multi-threading, and admin time per meeting.
- Map integrations (CRM, BI, meeting platforms) and lock success criteria in writing.
- Set a simple enablement plan: 30-minute kickoff, weekly office hours, one feedback loop with RevOps.
- Align on compliance (consent, recording notices), security, and data retention before rollout.
Metrics to watch during a pilot
- Discovery completeness (are key qualification fields consistently captured?).
- Next-step quality (clear owner, date, and outcome on every call).
- Time-to-first meeting for SDRs and stage-2-to-stage-4 conversion for AEs.
- CRM hygiene: percent of opportunities with updated close date, amount, and stakeholders.
- Rep time saved per meeting (prep + notes + CRM updates).
Questions to ask any real-time assistant vendor
- How does it adapt prompts to our methodology (e.g., MEDDICC, SPICED, or custom)?
- What data is written back to CRM, and how is field mapping managed?
- What security standards are in place (e.g., SOC 2) and how is call consent handled by region?
- Can RevOps configure playbooks without engineering support?
- What evidence do you have of sustained behavior change after 90 days?
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