Crew

Your most responsive contact feels like a champion. Steve Pascucci has spent a decade betting on someone else: the person in the corner of the room asking the hardest questions. Full episode with Steve is live everywhere! https://lnkd.in/erWSA6mG

if anyone ever drops the line “agentic workflows” in conversation, you can bet the mortgage they know absolutely nothing about AI

new episode of the Crew podcast w/ Steve Pascucci, VP of Global Sales @ Outtake, is officially live on Spotify, YouTube, Apple Podcasts, and our blog Outtake is the Series B, AI-native security company building the trust layer for the internet - backed by CRV + ICONIQ and recently named a Forbes Next Billion-Dollar startup before Outtake, Steve spent a decade at Cloudflare, where he was the first outside sales leader hired - he built the first sales teams, led the push into enterprise, and ran the global GTM for Zero Trust he's our first guest from a security background, and our first episode filmed on-site (Outtake HQ in Williamsburg - best view we've had yet) we got into: - why the champion answering all your emails is usually the wrong one to bet on - how cyber selling differs from SaaS: middle out, not top down, and the bimodal deal cycle - threat actors building pixel-perfect impersonations at machine speed - creating urgency without ambulance chasing when you can already see a prospect's exposure - Cloudflare lessons: mistaking good timing for a pattern + why he always took the scariest internal path - his hiring red flags, the best answer he's heard to "how do you use AI?", and why he's considering blocking AI tools for new hires in month one + much more give it a listen/rate/review/subscribe - assets in the comments

the Paraform talent density index came out this week - after speaking to thousands of GTM candidates and interviewing top GTM leaders, here are the ones building the most elite sales teams: note/constraint here - only putting the ones here I deem truly AI-native (only started to build their sales teams post chat-GPT launch in Nov 2022) + were mentioned in Paraform list (they named ~50 companies): - Anthropic - OpenAI - Modal - Decagon - Fireworks - LangChain - Together AI - Cognition - Harvey - Perplexity - Rogo - Mistral - Sierra - Clay - Parallel - Baseten - Cursor - Factory - ElevenLabs who else?

New episode drop of the Crew Podcast with Steve Pascucci (VP of Global Sales at Outtake)! His resume is a masterclass in building enterprise sales from scratch: Granicus → Cloudflare (the first outside sales leader they ever hired, pre-IPO through a $100B market cap) → built Cloudflare's enterprise motion → took Zero Trust global → now running global sales at Outtake as it builds the trust layer for the internet. This one is for enterprise AEs forecasting deals this quarter, sales leaders hiring in the AI era, and anyone trying to figure out how selling security differs from selling SaaS. Our key takeaways from the conversation: 1️⃣ The champion answering every email is probably the wrong bet. The strongest champion is the person in the corner of the room asking the questions that make you uncomfortable. They're thinking 18 to 24 months out. They know the plan. 2️⃣ The magic happens one level below the C-suite. Executives get things done through trusted lieutenants. Win the direct report who can zoom in and out on the business case, and the exec rarely says no. 3️⃣ Tie your deal to the 10-K. Buyers can spend money on endless things. The deals that close map to the priorities in the annual report and on your buyer's year-end performance review. 4️⃣ Create urgency without ambulance chasing. Outtake can find impersonations of any company on the planet. Steve still won't send them as a tease for a meeting. Share findings across a vertical, offer a deeper scan, and never put a buyer's back against the wall. 5️⃣ Don't mistake good timing for a pattern. One of Cloudflare's early lessons: a campaign that works once might just be timing. Pour resources into repeating it and you burn a lot of calories. Question your data before you scale it. 6️⃣ Hire people who get excited by the blank page. Some of Cloudflare's best early reps set appointments on Discord and spotted competitor meetings from Facebook check-ins. Technically curious people expand the walls of how you sell. 7️⃣ Screen for finishers. Every jumpy resume comes with great reasons to leave. Steve wants the other half of the answer: what would have needed to be true for you to stay? We learned a TON from this one. If you're selling into the enterprise in the AI era (or deciding which hard path to take next), you'll like it. Link in comments. 👇

Before you sign that startup AE offer, run the company through the same five checks we do. At our first live Crew Podcast in NYC, Curt Clauss, Partner at Crew, broke down what we look for before we ever put a candidate in front of a startup: 1. Is there a tier one investor attached? 2. Is the role predominantly inbound? 3. Is there real product market fit? You'd be surprised how often there isn't. 4. What did last quarter's deal mix look like, and who closed those deals, the reps or the founder? 5. What does their Slack wins channel look like? Cobwebs and crickets tell you everything. If a role can't pass these, the OTE on the offer letter doesn't mean much.

New episode drop of the Crew podcast, and this one's special: our first-ever LIVE episode! 🎾 We recorded it on a padel court at Reserve in Hudson Yards during our AI GTM Paddle Club, with ~150 of New York's best GTM operators in the room. The lineup: Curt Clauss (Harvey, Outreach, founding AE), Matthew Roberts (10 years of SDR leadership), and Cailen DSa ( Box → Dropbox, watched a company go $1M → $1B in ARR). Plus drop-ins from Mark Ebert (SVP of Revenue at Profound) and George Fullerton (Head of Sales at Basis). And of course, Chris Balestras! This one is for AEs weighing their next offer, sales leaders hiring in the AI era, and anyone with a strong opinion on whether "GTM" sounds bogus. Our key takeaways from the night: 1️⃣ Negotiate your offer. Don't over-negotiate it. Same rule for prep. Doing your homework on the hiring manager is a green flag. Listing the founders they went to high school with is a red one. Prep, don't creep. 2️⃣ Run the 80/20 before you take a startup AE job. Curt's baseline: a tier one investor, a mostly inbound role, and real product market fit. "You'd be surprised how often there isn't." Then look at last quarter's deal mix and who closed those deals. 3️⃣ Read the wins channel. Ask to see their Slack wins channel before you sign. Cobwebs and crickets tell you what the pitch won't. 4️⃣ Wiz ran a six-to-12-month enterprise sale in six days. That pace is the Wiz playbook OpenAI just brought in. If you're built for that speed, you've earned the paycheck. 5️⃣ "Four to five years at every job" is a big-company rule. Databricks' president calls short tenure a red flag. Chris puts the startup operator reality at two to three years. Five one-year stints in a row is a different story. 6️⃣ People stay for three reasons. They're hitting quota. They're learning from people they like. Their equity is growing and they're still winning deals in the field. Break one and the clock starts ticking. 7️⃣ "Money" is a fine answer to "what motivates you?" The story behind it decides whether you get hired. Wolf of Wall Street energy loses the room. Wanting to pay off your parents' mortgage wins it. We learned a TON from this one (and settled the padel vs. paddle debate once and for all. It's paddle). If you're picking your next rocketship or building the team that rides it, you'll like it. Link in comments. 👇

We got four sales leaders from AI-native companies in one room and asked what nobody tells you before you join one early. Jack on why equity is the wrong thing to optimize for. Todd on the worst 12 months of your life. Liam on the deal he made with his wife. Mark on the 3-year view. Full conversation is live now! #gtm #sales #startups

New episode drop of the Crew podcast, and this one's a first: four GTM leaders, one table, a lot of bourbon. Liam H. Mulcahy (Head of Go-To-Market at Parallel Web Systems), Jack Gashi (VP of Sales at Avoca), Mark Ebert (SVP of Revenue at Profound), and Todd Busler (enterprise sales at Clay). Combined, they're running revenue orgs that are hiring faster than their planning process can survive. We asked them what the job actually looks like right now, not in retrospect. This one is for founders making their first GTM leadership hire, VPs scaling past 50 reps, and anyone trying to figure out if they're at the right company. Our key takeaways from the conversation: 1️⃣ Annual planning doesn't survive contact with this hiring pace. Mark: you divide up the best accounts across five reps, then add twenty more people mid-year and they all need territories. There's no playbook for it. It's painful and it has to happen anyway. 2️⃣ Everything is written in pencil. A few things have to be written in pen. Liam's list of semi-sacred items: sales process, enterprise cycle length, expectations around paper. Everything else gets erased monthly. His favorite new absurdity: eval closes in two days, MSA takes four months, and founders think the deal is already done. 3️⃣ Enablement is now an arena, not a session. Todd's team built an enablement skill reps pull mid-call for competitive snippets. Jack hired SEs so AEs stop carrying the entire product in their head. Mark has two sacred blocks a week nobody can book over. When it's everywhere, reps have to actively choose not to use it. 4️⃣ Two companies, opposite answers on account management. Profound moved AMs into the sales org with quotas and club eligibility. Avoca killed the AM role and made AEs full-stack with TAMs owning renewals. Both are a week or two into it. Neither is sure. 5️⃣ The deal cap. Jack shuts reps off from inbound past a certain open-opp count. He'd rather give a deal to an AE with eight open than one with thirty, because eight is "I'm all over this" and thirty is "I'll get to it." 6️⃣ Forget the equity. Jack's take: for 90% of AEs, your equity is dwarfed by your W2. A company going from 75 to 200 is paying out real commission dollars. Go get a chunk of that three years running and the equity math takes care of itself. We learned a TON from this one. Link in comments. 👇