Zachary McCall

Hot take: Most leaders should measure SDRs with more of an emphasis on future potential. Most leaders look at things like: 🔬 Past quota attainment. 🔬 KPIs. 🔬 Conversion rates. Instead they should weigh more of: 🏋️‍♂️ Coach-ability. 🏋️‍♂️ Willpower and grit. 🏋️‍♂️ Impact of skills in the future. 🏋️‍♂️ Future business needs. 🏋️‍♂️ Cultivating strengths. The past is the past, look to the future of your people. What’s your SDR hot take?

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Olipop’s Rebrand Unlocked $500M Sales—Here’s How ** What made Olipop stand out in a crowded market? A simple, smart rebrand built to connect deeply. Here’s how they nailed it: ✅ 1. Focused on Their Mission → Healthy soda made approachable, not boring. → Their rebrand focused on joy, not restrictions. ✅ 2. Simplified Their Design → Clean labels with pastel colors and bold fonts. → Easy to spot, easy to remember. ✅ 3. Told a Relatable Story → They shared why they care about gut health. → Stories connect better than product pitches. ✅ 4. Aligned With Their Audience → Targeted health-conscious millennials. → Messaging felt personal and authentic. ✅ 5. Highlighted Their Unique Edge → Real ingredients, real benefits, no fluff. → They backed promises with proof. 💡 A great rebrand isn’t just about design—it’s strategy. Connect mission, design, and audience for real impact. ♻️ Reshare to inspire bold branding moves. 🔔 Follow Kai Brands for insights on building impact!

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Empathy is a vital step towards enhancing outbound strategies. Generic automated sequences are easy to tell apart and annoy customers. Sure automation tools are helpful, salespeople remain fundamentally human. Consider the client's interests and difficulties from their point of view. Collect information and create tailored strategies rather than sending out generic emails. Discuss actual business issues and provide workable answers. More relevance and less spam make all the difference.

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Absolutely agree! Unless you're in customer success, it's hard to grasp what CSMs handle daily. They must be consultants, sellers, product experts, industry gurus, relationship managers and incredibly patient - all to excel at their job. When I hear jokes about CS not doing much, it’s clear I’m dealing with someone who has no idea what it takes to run a successful business. To be a CSM, you need to be on your A game constantly, without rest. If you want the best in the industry protecting and advocating for your business, pay them accordingly. End of.

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How to add value when you're an AE selling into a new market: Sit in on as many calls as you can. - Implementation Meetings - Conversations with Prospects - Customer Success Calls Document all of the success, failures, and best practices. Package up that knowledge into digestible: - Emails - Videos - Posts - One Pagers - Cold Call Scripts Include a CTA to set up a 'free consultation' with your solutions team. Release that valuable content weekly to set a regular cadence. -- Remember, companies spend $25,000+ to join communities to connect with other professionals in their industry and share information. If you can condense that information and spread it... You're adding a ton of value even if you're not an expert.

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Sales people have some of the most variable comp of any W2 professional. Most comp structures are a 50/50 split, sometimes a 60/40 split (60% base and 40% variable based on performance). So my question for sales professionals - how do you think about your comp? Do you plan around your base income, OTE (on target earnings), or something in between? Since I started selling software almost 5 years ago, my family has decided to live off of my base. This has forced us to live within our means and helps avoid lifestyle creep as my income increases. This means my 401(k), our mortgages, rent, utilities, groceries, automated target contributions, and monthly variable expenses all fit within my base. With commission, I make a plan for the additional cash. Most of my comp plans have had quarterly commission payouts, so by the time the commission hits I have time to make my plan. My rule of thumb is 50% gets invested in my target account, 25% gets allocated to upgrades for our properties, and the remaining amount goes into our checking account as extra spending money. Sales reps, how do you think about your base vs variable comp?

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Our revops “team” at Chili Piper does A LOT OF automations. If you’d see our list, you’d think we have a full train of rev ops folks working here at Chili Piper (spoiler alert, we have 1 and a half). Here’s an example of an “unconventional” automation We assign churned accounts to SDRs. Yep, we automate outreach to churned accounts Here’s why and how First, let me tell you, it breaks my heart to see any customer churn. I feel like my heart is asking but always aim to learn from it and make everything better for them if they were to come back. Hence, we want to learn what made them leave, fix the problem, and win them back And the good news is that we win many of them back . Here are the nitty gritty on how we do this : We setup these rules for assigning churned accounts to our SDRs: – Account Status = updated to Churned – Transaction End Date = 91 days – Round Robin across SDRs and update SDR Owner – SLA: after 12 working hours, check if there was activity yesterday AND ROE phase ≠ unfit to work, send Slack notification – SLA: after 12 working hours, check if there was activity yesterday AND ROE phase ≠ unfit to work, reassign – Provide a Slack notification to the AM (80 days post-contract end date) – Provide a Slack notification to the SDR once the Account has been assigned (91 days post-contract end date) – Provide SDRs with information on why the account is churning in SFDC to give them the context to sell into the account effectively. If you are curious about more details on this, let me know!  

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The biggest difference between great sales reps and bad ones: How they bounce back from rejection. Early on in sales I had issues recovering from rejection. There are so many ways to de-rail your whole day. - Unresponsive prospects. - Deals falling through. - A rude prospect. - A bad call. - Etc… Those negative interactions can easily string into bad Days / Weeks / Months. Instead… Great reps do an awesome job of getting back to equilibrium. Might have a big win, or a big loss. But… They level out quickly from those emotional swings. Instead of dwelling, they focus on: - Look at what can be learned from each situation. - Reward yourself for the work, not the outcome. - Focus on things they can control. - Celebrate the small wins. - Think long-term. It’s an area that I’ve been working on this year. Look to get back to that baseline. ⚖️ Subscribe to my newsletter - Sales Synergy - 👉 Link in bio.

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Your Founding AE Will Make or Break Your Business—Ignoring Their Product-Market Fit Feedback? That’s a Fast Track to Failure Hiring a founding AE isn’t just about “filling a role”—it’s a high-stakes decision that can make or break your company. Think of them as your lifeline to the market. They’re not just selling; they’re the ones gathering real-time feedback on your Product-Market Fit (PMF), and ignoring their insights is like throwing away a roadmap to success. Here’s why their feedback isn’t optional—it’s critical: - They Know the Brutal Truth About Your Product - They’ll Define Success, Whether You Like It or Not - Scaling Without Their Insights? Good Luck - Competitive Intelligence You Can’t Afford to Ignore - Their Wins Validate Your Business Model The Harsh Truth: Ignoring Your Founding AE Is Self-Sabotage Your founding AE isn’t “just” a salesperson; they’re your closest connection to the market. Ignoring their insights on PMF is actively sabotaging your potential. Let their feedback guide you—it could be the difference between sustainable growth and an expensive lesson in what not to do.

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Should you move upmarket? Makes sense, right… Sales velocity is plummeting. Win-rates are down. Pipeline cvg is now 6-7x (instead of 4x). CAC is up. Burn multiple is being thrown around. AE’s self-prospecting is not filling the gap. Quota attainment is <40%. The concept of linearity is failing i.e double $$ revenue = double leads = double opps = double headcount Seems logical to off-set a decaying Sales Velocity with a nice big bump in ACV. But, before you rewrite ICP and revamp messaging, take a breath. Moving upmarket may not be the right move. Consider the following: ✅ Are you targeting the right customers with the right message in the right channels? ✅ Is CAC optimised? Should it be moved from sales to marketing? ✅ Can incremental improvements across funnel/bow-tie compound results? ✅ Is the buyer journey & sales process aligned to the nuances of your product/industry/persona (be honest 😶 )? ✅ Capacity and effectiveness: should you reassess GTM orchestration i.e GTM motion, headcount, capacity, productivity KPIs, tooling. ✅ Re-assessing PMF and talking to customers who’ve purchased the fastest, expanded the quickest, and delivered the highest LTV. Triangulate learning(s) for messaging, positioning, and marketing initiatives. Moving upmarket can be a fantastic growth strategy, but it's not a band-aid for underlying issues. Diagnose the root cause of slowing sales velocity and explore all options. It might be that a few tactical adjustments to your existing approach can put you back on track, or perhaps a strategic GTM realignment is needed first, and moving up-market (eventually) is about offence, rather than defence.

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It's not uncommon in fractional sales to come across orgs that are asking for 10-15x pipeline coverage. Sales is hard. Sales isn't THAT hard. Reality check: about 6% of sellers account for 92% of ARR, and they all run processes that look a lot alike. If you haven't cracked sales yet, you're not alone. In fact, you are the 94%. BUT you can use the same process as the 6% and dramatically increase your revenue for a hell of a lot less than it will cost you to 10x your pipeline.

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SaaS Sales: Lessons Learned from the Trenches SaaS sales isn’t just about closing deals—it’s about solving real problems and building long-term partnerships. One experience that stands out from my journey shaped how I approach every sales conversation. A prospect once told me outright, "We’re not interested." Instead of walking away, I took a step back and asked, "What’s your biggest challenge right now?" That simple question opened the door. They shared concerns about inefficiencies in their workflow. I listened, asked follow-up questions, and tailored the conversation to their needs rather than pitching features. The result? Not only did we close the deal, but they became one of our most loyal customers. This experience taught me some valuable lessons: 1️⃣ Start with empathy – Understand your prospect’s pain points before presenting solutions. 2️⃣ Focus on outcomes – People buy results, not features. Show them the impact. 3️⃣ Stay consistent – Rejections often mean “not right now.” Keep the relationship alive. SaaS sales is about more than revenue—it’s about building trust, delivering value, and ensuring your solution truly makes a difference. What’s a lesson or story from your sales journey that changed how you approach prospects? Let’s exchange ideas! 💬 #SaaSSales #CustomerSuccess #SalesLessons #B2B

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Our average sales cycle in mid-market is 3-6 months, and I’ve now closed 3 deals this year in under 24 hours. A buyer’s journey has a few core components: -Acknowledgment of a problem (why now) -Deciding it’s a problem worth investment versus status quo (why change) -Choosing one solution versus others (why you) All three of those can be fast-tracked under a unique situation. A previous user joins your account. They know their org has a problem without it, that it requires new technology, and that you are the best -in-market. It comes down to instant trust. Forget the 3 demos with 3 other vendors, reference checks, and research. Shoutout to UserGems 💎 for consistently bringing them to my inbox. Every org needs a strategy to retain their raving fans. Regardless of where their career takes them. P.S. If you want to see my UserGems email template, can grab here: https://lnkd.in/gaHQgRvt

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Losing control of deals is a killer. We run a 2 step next step setting process to ensure we always have time locked in and don't lose control of a deal: 1) Clear recommendation on next steps and the why behind a call. There's no "does it make sense to" or "would it work for you to..." ❌ . If you do this, you're asking a closed question that gives people an out. You need clear, concise next steps that sells on value e.g: "I'd recommend we get time on the calendar with X later this week to walk through a custom quote that is tailored based on Y - I'm free between 1 and 3 currently" ✅ 2) Sometimes you'll get push back on the first option - typically because they need to speak to another stakeholder or they need to be included on the call. Here we have a strategy that works 9/10 and goes something like - "okay no problem at all, my calendar is getting super booked so what I'd recommend is we at least have a placeholder in the diary. I'll throw some time in for next week and if the time doesn't work, we can always shift it around if needed." Even though this is just a placeholder, having a call in the diary typically will illicit a response and will get rescheduled to a time that works for everyones calendars. A lot of the time it just ends up getting accepted! Rather than just handing the keys to your prospect or sending over a calendar link that doesn't get used, this option means you aren't just chasing them constantly and keeps you in more control! 💫

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Some not-so-direct sales learnings about sales: - Teamwork >>> Solving all your problems yourself as an AE - Company goals & vision >>> Individual quota (mindset) - Health is wealth (revenue). Showing up half-asleep or hungover doesn't help at all! Yes, personal experience! - Long-term relationship with leads/clients >>> pressure of closing them this month/quarter. (Gotta ignore the pressure of closing them ASAP from leadership sometimes. Sounds harsh, but they thank you later) - Extroverts are overrated - Legal never helps (JK) - It's just like dating (not kidding) Disagree with any of them? #saassales #B2B

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How BAD pipeline reviews sound: "Whats changed since we talked last week?" 🤦‍♂️ Followed by covering non-strategic updates. Not poking holes in your deals like: - are we at power? - are we multithreaded? - do we understand their buying process? BUT at Gong 👀 My manager comes prepped. We get straight into it. "We're not at power...whats your plan?" I'm easily able to tell which deals are: - not likely to close based off historical trends within YOUR business 🧠 - exhibiting 🚩 behaviors over zoom/email. - single threaded. Dying to know what other people look for in their pipeline reviews? P.S. bonus points if you LMK what your forecast calls usually sound like 😉 P.P.S. These are just a few examples. Gong can flag any deal risk or weirdness that puts pipe at risk.

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