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Los Gatos, California, United States
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17K followers
500+ connections
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Articles by Brendon
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4 Startups I Love
4 Startups I Love
Amidst an ocean of hot takes about macro/micro economic and tech topics, there are actually quite a few awesome…
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8 Comments -
Who's Number One? (In the Sales Cloud)Oct 11, 2021
Who's Number One? (In the Sales Cloud)
Almost 4 years ago I spoke to a bunch sales leaders and had them rank their Sales Stack, most important to least…
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10 Comments -
What is the Risk to do Nothing?May 7, 2021
What is the Risk to do Nothing?
I often talk to founders and VPs of Sales about the risk/reward equation as it pertains to prospective customers. Both…
12
4 Comments -
Why Point Break EnduresOct 13, 2020
Why Point Break Endures
Few people thought much about a 1991 film release about an undercover FBI agent pursuing surfer bank robbers. It…
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8 Comments -
Who Should Be a VP of Sales?Jun 23, 2020
Who Should Be a VP of Sales?
I think it’s sucks that this needs to be pointed out, but it needs to be pointed out. In 20 years in tech, the number…
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7 Comments -
Just Because Your Scale VP Didn't Kill You Doesn't Mean you Should Have Hired HimJan 29, 2020
Just Because Your Scale VP Didn't Kill You Doesn't Mean you Should Have Hired Him
One of the most ill-defined, ill timed, and ill executed hires in the tech/saas/software space is the "Scale Sales…
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For ***** Sake Stop Bragging about Your Discovery CallsSep 18, 2019
For ***** Sake Stop Bragging about Your Discovery Calls
I'm a reasonable guy. But it's time to talk.
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38 Comments -
8 Great Sales Leaders (in 8 States, and 1 Desert) Who Can Make YouAug 19, 2019
8 Great Sales Leaders (in 8 States, and 1 Desert) Who Can Make You
90%. That's how many of you are not going to make it as a startup.
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9 Comments -
What's Old is New Again - Coming Full Circle (Silicon Valley Style)Aug 12, 2019
What's Old is New Again - Coming Full Circle (Silicon Valley Style)
Before there was Instacart, there was Webvan. Webvan is one of the most celebrated disasters in Silicon Valley History.
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Sales and The SpouseJun 4, 2019
Sales and The Spouse
We aren't normal. Us sales folk.
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14 Comments
Activity
17K followers
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Brendon Cassidy posted thisYes, people buy based on what’s in the best interests of the company. They also buy based on what’s in it for them. How does this help them if it works out? How does it create risk for them and their job if it doesn’t work? I’d say the individual motivation of the buyer matters more to them. They don’t want to look like an idiot for buying your shit. Most people never sell to the person, just the company Feels like missed opportunity.
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Brendon Cassidy posted thisThere are some really good early stage startups who have real tailwinds, PMF, and white space, who are not getting any investor attention. Like, good outcomes very real and even likely. The VC herd mentality has never been worse.
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Brendon Cassidy posted thisIn a bind: ask for help. We all have people around us who can and will help us. Most of us are too proud to help. Including me for most of my career. And if nobody wants to help you, it’s good motivation to start building relationships where you give as much if not more than you receive Help someone. Small. Big. Whatever Many today are so self serving they’ve lost the concept that relationships are reciprocal
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Brendon Cassidy posted thisOG sales leaders I’m a fan of, to name a few: Mike Earnest at Wiz; Parm Uppal at Chainguard; Austin Stefani at dbt Labs—although maybe that’s called Fivetran now; Jeff Perry , CRO at Carta; Jennifer Lawrence at RedPanda, Matt Gahr of ex Cornerstone and Spiff/Salesforce fame, Marc Jacobs , who has had success at a lot of places. I’d also include Matt MattMatt PlankPlank at Rippling, although I’m not sure I’d call him OG. He falls somewhere between the new guard and the OG category, but he’s certainly been massively successful in building Rippling. Then there’s the new guard—the new-era, up-and-coming sales leaders I’m a big fan of. I’d include Todd Busler at Clay; Walker Fitch at Artisan; Nick Casale at AirOps; Evan Cassidy at Decagon; Jack Gashi at Avoca; Alex Cramer at Cresta; Adam Ali at Rox, Jonathon Blackburn of Nooks/Lattice fame, Steve Smith at Canopy Connect; Mike Donahue at Maven AGI, Marchelle Renee Mooney at Mangomint, Josh Roth Gorgias, Jon Parisi at Tavrn AI, Ochart at Gong, and Mike Haylon at Numeric. Some are friends. Some are not people I know super well. All I have a lot of respect for. I know how hard the job is and it’s mostly between the ears.
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Brendon Cassidy posted thisYou’re gonna see a lot more Listen Labs scenarios. Good for them Smart play Get out on top
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Brendon Cassidy posted thisReal courage in venture means making a well-reasoned bet before it’s socially safe, then staying accountable for the reasoning—not just claiming conviction after everyone else has arrived. Tell you what…The latter is pretty much the norm at this point Very few in the former But those will be the real winners imo. Always been that way.
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Brendon Cassidy shared thisFastest to $1 billion in ARR in a PLG / consumer Ever An incredible company that Cassidy Ventures is proud to call a client.The Untold Story of Higgsfield | Burning $4M a Month on AI Models | CEO, Alex MashrabovThe Untold Story of Higgsfield | Burning $4M a Month on AI Models | CEO, Alex Mashrabov
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Brendon Cassidy posted thisA pretty good philosophy on hiring your VP of Sales: have they successfully done the job running and building a sales org where the conditions were more difficult than yours (less demand, lesser tailwinds, more competition) Some stage adjacency for now and the next 18 months helps too
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Brendon Cassidy liked thisBrendon Cassidy liked thisRay and I are back in the arena. Looking for stellar teammates. ----------------------- After a decade of building Affinity (CRM) and taking a break, Ray and I are back building a new AI company. More to come in a few months. In the meantime, we're hiring our first two sellers. I didn't anticipate writing this post just a quarter in, but the feedback from early customers has been electric. Positive comments every day, unprompted intros to other potential customers and we're having a hard time keeping up. So now we are building the early GTM team :) We're looking for the first couple teammates to build the early sales motion. Selling into the upper mid-market and lower enterprise, industry agnostic. What I'm looking for: - Unrelenting grit and a desire to win - Positivity and customer obsession that moves mountains - An elite seller who's been top of the leaderboard selling large transactions, and wants to build now - Ability to source pipeline and ruthlessly project manage the sales process - Early stage experience Why should you join us: - Not our first rodeo. Ray and I built Affinity into a global company and hired 500+ people along the way. We're going after something 10x bigger, and it will be career defining for the right people. - I have deep empathy for this job. I have done it, hired for it multiple times and I know how hard it is. I will be there with you in the trenches fighting hard to win. - Massive TAM - very few markets are as big as the one we're tackling. - We do have the usual things you'd expect: backed by the best investors, amazing office (yes, we have all the different kinds of water), etc. These roles are SF only, 5 days a week. ----------------------- If you've worked with us before, please repost to your network so the right folks can see it. And if this is you, DM me :)
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Brendon Cassidy liked thisBrendon Cassidy liked thisWe couldn’t be more excited to partner with Marriott International, Frid Edmond, and team. For nearly a century, Marriott has put people first, set the standard for guest experience, and embraced innovation. Continuing that heritage, Marriott is adopting Cresta globally across the customer journey: from an agentic front door and AI Agents across voice and chat, to intelligence across every conversation and agentic assist that helps associates serve guests. This is the next phase of AI transformation in CX: optimizing the entire customer journey, not just individual siloed interactions. Excited for what’s ahead. 🌊🌊
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Brendon Cassidy liked thisOG sales leaders I’m a fan of, to name a few: Mike Earnest at Wiz; Parm Uppal at Chainguard; Austin Stefani at dbt Labs—although maybe that’s called Fivetran now; Jeff Perry , CRO at Carta; Jennifer Lawrence at RedPanda, Matt Gahr of ex Cornerstone and Spiff/Salesforce fame, Marc Jacobs , who has had success at a lot of places. I’d also include Matt MattMatt PlankPlank at Rippling, although I’m not sure I’d call him OG. He falls somewhere between the new guard and the OG category, but he’s certainly been massively successful in building Rippling. Then there’s the new guard—the new-era, up-and-coming sales leaders I’m a big fan of. I’d include Todd Busler at Clay; Walker Fitch at Artisan; Nick Casale at AirOps; Evan Cassidy at Decagon; Jack Gashi at Avoca; Alex Cramer at Cresta; Adam Ali at Rox, Jonathon Blackburn of Nooks/Lattice fame, Steve Smith at Canopy Connect; Mike Donahue at Maven AGI, Marchelle Renee Mooney at Mangomint, Josh Roth Gorgias, Jon Parisi at Tavrn AI, Ochart at Gong, and Mike Haylon at Numeric. Some are friends. Some are not people I know super well. All I have a lot of respect for. I know how hard the job is and it’s mostly between the ears.
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Rachelle Green
ZoomInfo • 2K followers
ZoomInfo meets you where you’re working. 💫 Not only can you access ZoomInfo insights directly inside of Claude, but now you can do it without even leaving Slack. In this video, our CEO and Founder Henry Schuck takes you through how you can build a targeted prospecting list and account plan in under 5 minutes from Slack via Claude. Watch the full video and get started here: https://bit.ly/4coq43O
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1 Comment -
Paul Perrett
Firmable • 3K followers
The market for B2B sales tools is full of AI features that look impressive in a demo and don't change Monday morning. The ones that do are boring to describe and transformative to use. They remove a step that used to take 45 minutes. They make sure a trigger doesn't get missed because a rep was busy. They turn "we should probably follow up on that" into a task that already exists in the CRM. That's the version of AI worth paying attention to. We've been building toward this at Firmable for a while. AI agents that monitor the market for buying signals - leadership changes, funding rounds, hiring spikes, etc - and push them into your CRM automatically when they fire. Not a dashboard to check. Not another tab to open. But a task in HubSpot or Salesforce that says: this happened, here's the context, here's who to call. The sales teams that figure out this kind of AI first won't just be more efficient. They'll be having conversations their competitors don't even know they should be having. That gap will be obvious within 12 months. I'd start closing it now. #aisalesintelligence
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Kevin Morgan
Morgan Executive Search LLC • 9K followers
AEs are not short on activity. They are short on precision. In the last few months, I have seen this pattern repeat across multiple CRO searches in PE-backed SaaS. Reps are running full schedules, logging calls, moving deals. But the pipeline does not reflect it. Stages are inflated, next steps are vague, and qualification is optimistic at best. The issue is not effort. It is inspection. Three things that separate the teams getting this right: • Clear exit criteria at every stage, enforced by the manager, not just the rep • Next-step ownership confirmed before the call ends, not after • ICP discipline that kills bad-fit deals early instead of carrying them for two quarters The CROs who are winning in this market are not running more campaigns. They are tightening what counts as a real opportunity. Inspection beats motivation speeches. What is the one inspection metric you trust most right now?
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Rafael J.
Ollama • 6K followers
Reminder for MM AEs: buyers *appreciate* when you are prescriptive with your process (how they evaluate your product, how you engage evaluators). They already have a million things going on. Optimizing how they run an evaluation cycle (who to loop in when, what to test for at what time, whether to do X or Y and when) of a novel technology, particularly a new category of tech, is something they will generally love to offload to a sales team... in fact, they expect you to do so. This a large part of why you have a job (being an outsourced, assertive project manager), and the sales teams who are more prescriptive with them, educating them on how to evaluate this type of tech and what resources are available from your side or not, while maintaining a *trusted advisor* level of rapport so they feel safe to follow your lead, will steer how they evaluate all their options... yours and the competition. Take advantage of this and be (respectfully) dominant & prescriptive in your conversations with them, while keeping it clear you're 100% looking out for the best outcome for them, be it with your product or not. The art of doing this is one of the arts of sales. The only time this isn't the case is if you're selling to a uniquely organized team, often only found at larger Enterprise accounts where there's an RFP process and a team of evaluators who have careers doing this with new technology and are stubborn about how they run their process. And even then ... If anyone disagrees, I'd be curious to learn why.
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Derek Rahn
LeadGenius • 13K followers
Here’s the dirty secret no one at your next RevOps conference will admit: Your “cheap” data is bleeding you dry. Every time your SDR chases a ghost lead from a bulk database, you’re lighting money on fire. Every time your LLM trains on outdated contact info, you’re teaching it to hallucinate. GTM leaders love to brag about database size. But static data isn’t a moat — it’s a mirage. The future belongs to bespoke data — living pipelines that adapt in real time, powered by contextual signals, human verification, and AI that actually learns from the world as it changes. Stop buying prebuilt sludge. Start owning your GTM fuel. 🧠 The future of GTM data isn’t bulk — it’s bespoke.
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Matt Green
Sales Assembly • 66K followers
Your AEs are sitting around waiting for SDR meetings while their pipeline coverage drops < 2x. And you're wondering why forecasts keep missing. The linear SDR-to-AE model assumes clean handoffs and qualified pipeline flowing upward on schedule. But markets are tighter now. Budgets are frozen. Decision cycles are longer. You CANNOT afford to depend on a single pipeline source. Parallel prospecting should be, with few exceptions, not even up for debate right now. Here are some standards to set in stone: 1. SDRs focus on top-of-funnel volume. Book meetings. Qualify interest. Create awareness in accounts that aren't actively buying yet. 2. AEs prospect their own territory. Hunt for warm referrals. Expansion opportunities. Build relationships with execs. Go after high-value targets that require account context and business acumen. 3. Execs (yes, you) support in relationship-building Board members, founders, C-suite: everyone participating in opening doors and accelerating deals. Don’t get me wrong - this is NOT about SDRs failing. It's about current market conditions requiring more pipeline from more sources. Some of the best sales teams I know moved away from mass outreach this year and leaned into their network. Asked for referrals. Re-engaged relationships from 2-3 years ago. Fewer touches but higher quality deals. Better logos. Larger ACV. PS - Few teams I know use Vieu to uncover who in the company network (investors, advisors, customers, execs etc.) is connected to target buyers and can make intros. Check it out here: https://lnkd.in/g9GB2J8u That's AE-level prospecting. That requires business relationships and strategic thinking that SDRs typically don't have access to yet. The pushback usually sounds like: "But that's what we pay SDRs for. AEs should be closing, not prospecting!" lol ok. How's your pipeline coverage looking right now? If your AEs only work SDR-sourced pipeline, they're dependent on a single source. The implementation is straightforward: - Adjust quota expectations. If AEs spend 20-30% of their time prospecting, quota reflects that or territory size decreases. - Comp structure rewards it. Higher commission rates on self-sourced deals. SPIFFs for expansion within existing accounts. - Track pipeline composition. What percentage is SDR-sourced vs. AE-sourced? If it's 90/10, your AEs aren't really prospecting. - Get the right tech: Vieu for scaling network-led intros, Clay for market signals etc. This doesn't eliminate SDR teams, but it does admittedly change how they work with AEs. In a good way, IMO. Less handoff friction. More collaboration on account strategy. SDRs opening doors, AEs building relationships. Your top performers already do this. They're not waiting around for their next SDR meeting. They're working referrals, reaching out to warm contacts, expanding existing accounts. Make it systematic across the whole team.
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Martin Roth
Filmore • 13K followers
Executives won't open cold emails, but they will open a package. This is my best advice for breaking into Tier 1 accounts... When we were trying to break into big enterprise accounts at Levelset, there was one approach that consistently worked. We sent our top prospects a gift in the mail. Most teams never try this. They send another cold email, another LinkedIn message, or another voicemail. Then they sit around wondering why nothing converts. When you’re going after companies that can change your trajectory, you have to operate differently. Start with the person you are trying to connect with. Before you buy anything, spend time learning about the prospect. Look at what they post. Notice what they care about. Listen for the problems they’re trying to solve. You’d be surprised how often people leave clues out in the open. AI is really helpful at pulling this together for you. It's important to understand what would actually matter to them. Pick a gift that shows you pay attention. It takes more effort to pick something thoughtful than it does to spray a thousand people with the same sequence. But you’re not going after a thousand people. You’re going after the handful who can meaningfully move your business forward. It doesn’t need to be expensive. It needs to be personal. Somewhere in the $25–75 range is enough to show you cared without feeling transactional. Include a handwritten card. Keep it simple. Three or four sentences. Tell them why you chose the gift. Tell them what it made you think about in their business. Then make a clear, easy ask. When everything else in their stack is automated, a handwritten note stands out. Send it in a bubble mailer. Nothing fancy. USPS works fine. A bubble mailer gets opened. People are curious. Just make sure the address is right. We double checked every single one. Full up after it arrives. Don’t assume they saw it. Don’t assume they connected the dots. Send a short email. “Just shipped you something. Should arrive this week.” Then follow up again after it lands. The follow up is where the meetings get booked. Did this work? At Levelset, this was our most reliable way to break into large accounts. The response rates were dramatically higher than anything we did through email or phone alone. And it wasn’t because we were clever. It was because we were willing to put in more effort than everyone else. Most reps won’t spend thirty minutes researching a prospect or writing a card. That’s fine. The ones who do will win the meetings with the best prospects. The Reality This work doesn’t scale. It’s not supposed to. You don’t run this play for your entire TAM. You run it for the hundred companies that would meaningfully impact your business if you earned their trust. For those accounts, a thoughtful gift is a small investment compared to the upside. And if you’re willing to do the work, you’ll end up in conversations your competitors never even get close to.
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