Warm leads & AI outreach: the future of B2B SaaS sales with Maximus Greenwald @warmly.ai

saas.unbound is a podcast for and about founders who are working on scaling inspiring products that people love, brought to you by saas.group, a serial acquirer of B2B SaaS companies.

In episode #32 of season 5, Anna Nadeina talks with Max, founder of Warmly, an AI-driven sales platform designed to help businesses identify and engage their most promising leads.

Max’s path to Warmly started with coding, hackathons and a stint at Google Maps as a product manager. After leaving Google he and co‑founders launched multiple startups — “we built the world’s worst product… then the second worst” — iterating through eight pivots over three years before landing on Warmly.

Fast forward: Warmly now serves roughly 400 paying customers and is approaching $5M in ARR. The team learned the hard lessons of product/market fit and settled on a core mission: help customers find revenue by delivering highly relevant lead lists and automating outreach.

What is Warmly — the core idea

Warmly’s value proposition is succinct: get you warm leads. That means turning anonymous website visitors and other signals into prioritized, actionable prospects and then helping you reach them through omnichannel outreach.

• Lead discovery: deanonymize website traffic to surface the company (and likely contacts) behind visits, filter out bots and low-fit accounts, and generate prioritized lead lists.
• Lead scoring & filters: score visitors against your ideal customer profile so the highest-propensity accounts rise to the top.
• Outreach automation: automated email and LinkedIn sequences, a website AI chatbot that can engage visitors in real time, and integrations into CRMs and sequencers.

How Warmly actually finds and engages leads

Warmly’s approach is twofold: data + orchestration.

Deanonymization and intent signals

Warmly observes website behavior (pages visited, mouse movement, session activity) and uses web scraping and data sources to map sessions to companies. Where privacy rules permit, Warmly can also suggest likely individual contacts at that company — a shortlist you can reach out to.

Warm calling — calling while someone is on your site

One standout capability is “warm calling”: when a high-value visitor is actively browsing your site, Warmly can proactively surface a chat/video widget and let a rep (or a bot in some cases) engage them in real time. According to Max, warm calling has a roughly five‑times higher pickup rate than traditional cold calling (cold call conversion to meeting sits around ~1–2%).

Orchestrator — multichannel outreach that plugs into your stack

Warmly’s Orchestrator pushes leads into existing email/LinkedIn sequences or a CRM. It hooks into sales reps’ actual inboxes and sequencers (Outreach, SalesLoft, Apollo, HubSpot, etc.), so outreach is sent from the rep’s address and follows pre-defined sequences. This keeps workflows familiar while automating lead delivery and timing.

AI in sales: what will (and won’t) be automated?

Max breaks down the sales motion into two primary tasks: (1) get someone to take a meeting (top of funnel), and (2) close the deal. His perspective on AI’s role:

• Top of funnel (lead generation & email outreach): largely automatable. Max predicts email will be handled by AI bots within months — drafting, sending and replying autonomously. Companies are already experimenting with automated sender aliases to run high-volume sequences.
• LinkedIn: currently still human‑centric because it’s tied to human profiles, but AI will increasingly assist and likely automate many parts over time.
• Calling: constrained by consent and regulatory concerns. For outbound sales calls you generally still need humans (and many people find cold AI calls creepy). Inbound/customer support calls are already moving to human‑indistinguishable AI voices and are likely to be automated extensively.
• SDR role: AI SDR tools are improving, but models and data quality are not yet good enough to fully replace human judgment and calling for many B2B contexts.

“Email as a channel is going down in terms of reply rates. The only way to combat that is to increase volume — or be hyper‑personalized — and AI can do both.”

GDPR and privacy: how Warmly handles European visitors

Under GDPR Warmly cannot always disclose the name and email of an anonymous website visitor. Their approach:

• Always reveal the company associated with a visit where permissible.
• Provide a ranked list of likely contacts at that company (CFO, VP Finance, etc.) from other databases, so sellers can reach out to the right people without claiming the visitor’s exact identity.
• Be transparent about probabilities: Warmly recommends contacting the likely contacts rather than asserting which specific individual visited.

Maintaining brand voice and personalization

Max emphasizes control over messaging. Instead of relying on individual reps to invent outreach copy, Warmly recommends that sales or marketing leaders author the sequences so messaging remains on-brand. Reps should personalize higher-value or account‑specific touches while automated sequences handle light-touch nurture.

“The best way to preserve brand voice isn’t to trust every rep to speak for your brand — let your sales or marketing leader write the copy and make reps use it.”

Warmly’s internal AI — engineering and enablement agents

Warmly has launched internal AI agents (for engineering and sales enablement) trained on their internal corpus: call recordings, Slack, emails, docs and help center content. These agents:

• Pre‑draft ~90–99% of code for engineers (human engineers review and finalize).
• Answer internal sales questions by surfacing prior conversations and best responses (95% accurate currently).

Max is deliberate about keeping customer‑facing support human for now, acknowledging he can tolerate internal glitches but wants more maturity before deploying AI into public support channels.

Tools Max mentions (and why they matter)

• Codegen: an AI engineering assistant that can dramatically speed up development by prewriting most of the code for a requested feature.
• Limitless: a wearable “always‑listening” transcription device that captures your day and makes it searchable — useful for action items and remembering details about people and meetings.
• Other tools discussed in the episode include email blockers or “gated” inbox services that filter cold reachouts — a reminder that recipient behavior will push outreach practices to be more thoughtful.

Building in public and fundraising decisions

Max publishes monthly revenue updates and a candid “Going Clear” series on LinkedIn, sharing wins, mistakes and learnings. That transparency helps him get fast feedback (a recent example: community feedback led him to change unpaid intern plans to paid).

On exits and offers: Max turned down a private equity acquisition approach because his investors backed the company to pursue big upside, not a modest early exit. He sees options — including partial sales models — but prefers to pursue a Series B growth path to deliver a larger outcome for shareholders.

Big wins, failures and evolving leadership

• Biggest win: closing a roughly $500k deal with a Fortune 10 company — a validation of product-market fit at scale.
• Biggest failure / learning: early mishandling of firings. Max now favors a humane, conversational approach: present the performance issue, offer options (PIP, immediate departure with severance, ramp‑down period, etc.), give the person time to decide and lower the temperature of the interaction.

Founder hack: the “number one priority” spreadsheet

Max’s practical companywide productivity hack is simple: every person lists their single number‑one priority each week (and indicates whether the prior week’s priority was achieved). It’s fast to scan and keeps the whole org aligned on the highest‑impact work.