Sample Submission: Driftwood

Founder 1 - Name & Role

Nadia Okafor, CEO

What have you personally seen, done, or experienced that led you to this problem?

I spent 6 years building and running recruiting at Ridgeline, a Series B fintech startup in New York. When I joined we were 30 people. When I left we were 210. I hired or managed the hiring of about 140 of them.

The thing nobody tells you about scaling a recruiting team is that the hardest part isn't sourcing. It's coordination. By the time we hit 100 employees I had two recruiters and we were collectively spending 15-20 hours a week on scheduling alone. Not screening candidates, not closing offers. Scheduling. Moving calendar blocks, chasing hiring managers for availability, rebooking when someone's flight got delayed or a panel interviewer called in sick.

I tried every tool. Calendly helped for first-round screens but broke down for multi-stage loops. Greenhouse managed our pipeline but had no real scheduling intelligence. We built internal Slack bots, wrote Zapier automations, even had an intern whose primary job was coordinating interview panels for engineering roles. None of it worked well enough.

The last straw was Q3 2024. We had 22 open roles and our average time-to-schedule for an onsite loop was 6.8 days. Not time-to-hire. Time to get the interview on the calendar after the candidate said yes. We lost 4 senior engineering candidates that quarter to companies that moved faster. Two of them told us directly: "Your process took too long."

I left in August 2024 convinced this was a solvable problem that nobody had prioritized because it feels like logistics, not strategy. But at scale, scheduling speed is hiring speed.

Founder 2 - Name & Role

Sam Reeves, CTO

What has Founder 2 personally seen, done, or experienced that led them to this problem?

Sam spent 5 years as a senior software engineer at Oakbridge, a mid-stage HR analytics startup in Boston. He built their core scheduling and calendar integration infrastructure, working directly with Google Calendar, Microsoft Outlook and iCal APIs. He's deeply familiar with the technical complexity of calendar systems: timezone handling, recurring event conflicts, multi-party availability windows and permission scoping across organizational calendars.

We met through a mutual friend at a founders dinner in September 2024. I was describing the scheduling problem and Sam's immediate reaction was "I literally built the backend that's supposed to solve this and it doesn't work because the product layer never understands what recruiters actually need." We started working together in October 2024.

Sam doesn't have recruiting experience. He's never run a hiring loop or managed a candidate pipeline. But he's built calendar infrastructure at production scale and understands the API-level constraints that make multi-party scheduling genuinely hard. The gap between "technically possible" and "actually works for a recruiter juggling 15 open roles" is where we're focused.

One-sentence description

Driftwood is an AI recruiting assistant that handles interview scheduling, candidate coordination and reference checks for in-house recruiting teams, so recruiters spend time closing candidates instead of chasing calendars.

Location

New York, NY

Started

October 2024

What problem or opportunity are you going after?

An in-house recruiter at a 100-person company managing 10-15 open roles spends 30-40% of their week on coordination work: scheduling interviews, rebooking cancellations, sending prep materials to candidates, following up with hiring managers for scorecards and chasing references. At a fully-loaded cost of $85,000/year for a mid-level recruiter, that's $25,000-$34,000 per recruiter per year spent on tasks that don't require judgment.

The real cost is harder to measure but more damaging: slow scheduling kills your close rate. Based on data from our 4 pilot customers, the average time between "candidate says yes to an interview" and "interview actually happens" is 5.2 days. For multi-stage loops with 3+ interviewers, it's 7.8 days. Every day of delay increases the chance the candidate takes another offer or loses interest.

Fieldstone Partners, one of our pilot customers, tracked this explicitly: they lost 6 candidates in Q4 2024 who cited "process speed" as a factor. At a blended cost-per-hire of $15,000 for their roles, that's $90,000 in wasted recruiting spend in one quarter.

The problem compounds as companies grow. At 50 employees, scheduling is annoying. At 150, it's a full-time job. At 300, it's a team. And the tools available today either solve the easy case (one-on-one scheduling via Calendly) or manage the pipeline without touching the scheduling problem (Greenhouse, Lever).

What are you building? Walk us through what a customer actually experiences.

A recruiter opens Driftwood and sees their active candidates organized by urgency: who needs scheduling, who's waiting for scorecards, who has a deadline approaching. Think of it like a recruiting command center focused on the next action for each candidate.

When a candidate advances to the next round, the recruiter clicks "Schedule" and tells Driftwood the interview format: "technical screen with one backend engineer, 60 minutes, remote." Driftwood looks at the interviewer pool, checks real-time calendar availability across Google or Outlook, filters by interviewer qualifications and load (so the same 3 engineers don't do every interview) and proposes 3 time slots to the candidate via email.

The candidate replies, picks a slot or suggests alternatives. Driftwood reads the reply, confirms the booking, sends calendar invites to everyone, attaches prep materials to the candidate's invite and adds scorecard reminders for after the interview.

If someone cancels, Driftwood automatically proposes replacement times without the recruiter lifting a finger. If scorecards are overdue, it nudges the interviewer directly. If a candidate hasn't heard back in 48 hours, it flags the recruiter.

The recruiter stays in control of all decisions. Driftwood handles the logistics.

Why is now the right time?

Three shifts in the last 18 months.

First, LLMs can now reliably parse natural language scheduling preferences from candidate emails and Slack messages. "I'm free Thursday after 2pm but not Friday" used to require structured input. Now the system can read it directly. This is the core unlock: the candidate doesn't need to use a tool. They just email normally and Driftwood understands.

Second, remote and hybrid work made scheduling dramatically harder. When everyone was in the office, you could walk to someone's desk. Now a 4-person interview panel might span 3 timezones, 2 calendar systems and a mix of in-person and Zoom preferences. The complexity jumped and the tools didn't keep up.

Third, the ATS market is consolidating around pipeline management (Ashby acquiring ModernLoop, Greenhouse cutting features, Lever's stagnation under Employ). The scheduling and coordination layer is being deprioritized by the platforms that should be solving it. That creates an opening for a focused tool.

Who are you building for right now?

In-house recruiting teams at Series A and B tech companies in New York City with 50-200 employees and 2-5 recruiters.

What progress have you made so far?

• October 2024: Started building. Sam joined as co-founder.
• December 2024: MVP complete. Core features: calendar sync (Google and Outlook), AI-powered scheduling proposals, candidate email parsing.
• January 2025: First pilot with Fieldstone Partners (85 employees, 3 recruiters, 12 open roles). Free pilot.
• February 2025: Added 3 more pilot accounts (65-140 employees each). All free pilots.
• March 2025: 127 interviews scheduled through Driftwood across all 4 accounts. 23 reference check outreaches sent.
• Key metrics: average time-to-schedule dropped from 5.2 days to 2.1 days. Recruiter self-reported time savings of 8-12 hours per week.
• No revenue yet. 2 additional companies on the waitlist for April onboarding.

Who are the existing players in this space?

• GoodTime: The most direct competitor. AI-powered interview scheduling. Strong product but enterprise-focused: minimum contract $30,000/year, 3-month implementation. Our entire target segment is priced out.
• ModernLoop: Was the closest competitor for our segment. Acquired by Ashby in 2024. No longer available as a standalone product.
• Calendly: Handles one-on-one scheduling well. Falls apart for multi-person interview panels, has no recruiting context and no ATS integration.
• Greenhouse, Lever, Ashby: Pipeline management tools. All have basic scheduling features but none handles multi-party coordination or rescheduling well.

Product stage

Private beta with select customers

Total funding raised

$0 (bootstrapped)

Currently raising

$1M - $2.5M

Use of funds

We're raising $1.5M pre-seed:

• 12 months of runway for Nadia and Sam (full-time)
• One additional engineer (calendar integrations and AI pipeline)
• Convert pilot customers to paid, acquire 15-25 paying accounts
• SOC 2 Type I certification
• 2-3 recruiting industry events

Target milestone: 20 paying accounts, $8,000-$12,000 MRR, SOC 2 certified by end of 2025.

Two things worth flagging. First, our pilot customers have all connected their Google Workspace calendars to Driftwood, which means we have read/write access to employee calendars. We take this seriously: all calendar data is encrypted at rest, we have a clear data retention policy (delete within 30 days of account closure) and we're starting the SOC 2 process in April. But we know this is a trust barrier, especially for companies with strict IT policies.

Second, Sam and I have been working together for 8 months. It's a newer co-founder relationship than either of us would prefer. So far the dynamic has been strong: I own product direction, customer relationships and go-to-market; Sam owns all technical architecture, infrastructure and AI pipeline. We haven't had a significant disagreement yet, which could mean we're aligned or could mean we haven't been tested. We're being intentional about it.