Jake Reni

Top 5 key metrics I recommend CROs use for inside sales professionals: 1. Speed of response 2. Efficiency of progression through the process 3. Number of calls per day 4. Number of positive outcomes 5. Demo sets As a CRO leader, these are five metrics that I live by. 

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Simple analogy: fly fishing is like #customersuccess and sales. Fly fishing requires patience, strategy, and preparation. So does driving meaningful customer outcomes. Patience: fishing and customer outcomes both take time. Rushing rarely delivers desired results. It’s about understanding the waters you’re in and finding the right moment to engage. Targeting: casting aimlessly doesn’t work. In fly fishing, you study the water, shadows, and movement of fish. In Customer Success, it’s about identifying the right opportunities to add value, focusing efforts where they will make the biggest impact. Fly selection: fish are picky, and their preferences change multiple times each day, let alone each season. You’ll have little success if you cast a bunch of random flies. Customers don’t want every fly in your box. They want what they need. Plan your approach through insights, engagement strategies, or customized solutions to find exactly what that is. Having the right tools: from the appropriate rod and reel to well-tied flies, the right tools make all the difference. In Customer Success, the tools might be CRM platforms, data analytics, or streamlined processes, but their role is the same: enabling you to execute effectively and deliver results. Managing Competition: A crowded river can mean fewer bites. Fish become wary when there’s too much traffic. Similarly, when customers are overwhelmed by competing voices or being over-contacted, they can disengage. It’s critical to find the balance: respecting their space, offering value when it’s needed and ensuring your approach stands out for its thoughtfulness and relevance. Fly fishing teaches us that success isn’t random, it’s the outcome of thoughtful preparation, targeted action, and consistent execution. Whether on the river or in the professional landscape, the principles are the same: patience, precision, and the right tools lead to meaningful outcomes.

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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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Who's your favorite CMO / VP Marketing in Austin? We (the Exit Five team) are traveling to Austin in November for a team offsite, and we're going to host a meetup (happy hour, networking, etc.) I'd love to do a fireside chat with a B2B CMO for this event, but I'm not plugged in down in Texas. So: who's your favorite CMO in Austin? Who should be on my list to reach out to interview for a live podcast / Q&A with 100 B2B marketers in November?

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How much pipeline gets left behind when your reps aren’t available? Do you know? When we talked with NextGen Healthcare, we learned that they were missing 1400 chats due to high volume and not enough coverage. There are two choices in this scenario: Hire more SDRs Or Scale with an AI SDR like Piper NextGen chose not to increase their headcount budgets and instead hire Piper the AI SDR to scale their inbound pipeline generation. Since hiring Piper earlier this year, NextGen has successfully closed that coverage gap and missed ZERO chats, leading to an additional $60k in potential revenue they never knew they were missing. . Read more about NextGen’s success here: https://lnkd.in/g_XHJd7q

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Connect the dots..... between People Process Product Technology & Business Unit Economics. There's no magic bullet. It's that simple and that hard. Over the past few weeks, I've had this conversation on repeat with Founders, CEOs and other GTM leaders. It's like Groundhog Day living rent free in my head. What's on repeat in your world?! #GTM #leadership #revenuegrowthengine

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My buddy got an Enterprise AE gig with ZERO sales experience. It's with a publicly-traded HealthTech company valued at $989M. Their sales cycles require a high-level of clinical acumen. Which is a major reason they hired him (former RN). They understand sales process can be picked up quickly... ...the key is having strong domain expertise / buyer persona knowledge. That doesn't mean selling fundamentals are irrelevant though. So I've been showing my buddy basic outbound workflows. He's found one especially helpful that I wanted to share. It's a great way to streamline LinkedIn engagement in your BoB. You just need two low-cost tools: - LinkedIn SalesNavigator ($99 / Month) - PhantomBuster ($69 / Month) The first lets you build targeted contact lists. The second automates your LinkedIn outreach to them. Before everyone roasts me in the comments. Let me clarify something important. This workflow ISN'T meant to be a spam cannon. It's meant to be a more personal engagement channel outside of email. So in my buddy's case, I recommended a play like this: 1. Sync his SalesNav with his SalesForce 2. Create a SalesNav Account Search based on his BoB 3. Within this Account Search, identify top contacts by title 4. Filter those titles by his territory geo (i.e. Florida) 5. Enroll his top contacts in a 4-step cadence This is what the messaging looks like: STEP 1️⃣ - Connection Request with no note (data shows a custom note with your connection request doesn't actually increase acceptance rates) STEP 2️⃣ (Wait 3 Days) "Hi FIRST NAME, I'm going to be in your neck of the woods visiting a few customers and wanted to introduce myself as COMPANY NAME'S new account rep. Thought we could grab lunch and tour your facilities if you're up for it. What'd you think? STEP 3️⃣ (Wait 3 Days) "Making sure my last note didn't get buried^^. Not looking to sell you anything. Just building relationships with customers in the area and wanted to treat you to a nice meal. Let me know your go-to spot and we'll get it on the calendar!" STEP 4️⃣ (Wait 2 Weeks) "Missed seeing you while I was in town! I should be back in the area soon and will shoot you a note so we can try to find a time to get together. Always available as a resource if anything comes up sooner!" Not every rep gets budget for customer on-sites. But if you do, this play is a no brainer. Even if the customer can't meet in person... ...you still have a compelling conversation starter. And these days, that's worth more than we realize. What other sales tips / hacks would you give my buddy? Drop a comment below 👇

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3️⃣ reasons why retention must be more emphasized in vSaaS. 1️⃣ Winning the Control Point This is foundational table stakes to the vertical SaaS playbook. There’s no expansion opportunity if you churn customers here. Winning the Control Point is your anchor that opens up the multi-product play that will eventually grow your ARPA. 2️⃣Setting Up Multi-Product In order to deepen the anchor, and become the operating system of your accounts, both in workflow and data, product education and customer marketing are a must. Marketing has to be able to convey brand narrative and messaging that shows a roadmap to a seamless workflow and operation if surrounded by your ecosystem of products. 3️⃣ Extending the Value Chain The pinnacle of the vSaaS business model, according to David Yuan, is being able to sell to different stakeholders both forward and backward. You can never achieve this pinnacle if retention is not one of, if not, the top metric for marketing post-acquisition. Marketing no longer stops at pipeline generation, but now will be integral in shaping a future narrative that builds demand for your product ecosystem. Shoot me a DM if you want to go deeper into the topic and see what this looks like in practice! #RevenueEngineering #GTM #VerticalSaaS #DemandGeneration #Evron #vSaaS

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Going to HLTH next week? Mark your calendar for Tuesday to come hear me and other industry experts talk about selling to employers in today's environment. Here's the details: ----- Location: Disco Stage Date: Oct. 22 Time: 2:20 – 3 pm PT Other speakers: John Zutter with Employer Direct Healthcare, Will Porteous with Maven, and Elizabeth Mitchell with PBGH. Moderator: Chrissy Farr Title: Is selling to employers still viable? Description: The self-funded employer market once shimmered like a golden opportunity for startups. But the economic climate has shifted and wallets have tightened. Inflation and point solution fatigue have left employers drowning in a sea of vendors, each promising to be the silver bullet for health care costs and employee satisfaction with little concrete evidence to prove their ROI. So is selling to employers still financially viable for digital health companies? As more prominent players venture into the employer realm, the long-term sustainability of this model should be debated. Amidst intense competition and a cluttered market, new entrants are finding it increasingly difficult to match the capabilities of established incumbents. Hear the challenges from both perspectives– employers grappling with an overwhelming array of options, and vendors navigating this tricky, oversaturated space. Join top health leaders to debate the economics, evolving needs of employers, and strategies digital health companies are employing to stand out in a crowded field. Remember, not all that glitters is gold – sometimes it's just the reflection of a thousand pitch decks vying for the same employer customer.

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CS teams NEED to start "managing up" with execs and the board by talking about REVENUE. Yes, you can keep talking about sentiment and feelings, but start with the $. Don't lead with churn- Bottom-line-focused execs don't like that headline, so you need to tell the story better. An informal poll had CS teams owning over 50% of the revenue of many SaaS companies. Lead with this and have it be your first talking point. From there you will be able to get more things done with other departments, as your requests will be revenue-focused Need to get a Customer Success Platform as you scale? Point to revenue and the potential to lose revenue without efficiencies Need to hire more to prevent burnout? Point to Revenue potential with renewals and upsells Talk in the language your execs and board want to hear.

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Why Fractional Work is a Perfect Fit for Many B2B SaaS Sales Executives 🚀 Ever wondered what it feels like to have total control over your career? After years in B2B SaaS sales, I’ve found that fractional work is one of the best ways to transition into working for yourself—or even starting your own business. Here’s why: I get to choose WHAT I work on: No more projects that don’t align with my strengths or interests. I focus only on what I do best. I get to choose WHEN I work: Whether it's busy or slow, I have the flexibility to align work with my life and homeschool. I make my own schedule. I get to choose WHO I work with: I collaborate with clients and teams that align with my values and goals—no more mismatches. I get to choose WHY I work: I know I'm blessed to have a spouse providing benefits and I also know I'm working to make something for my family. I get to choose HOW I work: Every process is designed around my style, allowing me to deliver the best results efficiently. I get to choose WHERE I work: Who cares my location so long as I crush it. I have a car and a zoom too lol I get to say NO: Turning down work that doesn’t fit my goals or priorities has been empowering. No pressure to compromise ethics to keep a job. I get to say YES: The freedom to take on opportunities that excite me means I’m always engaged in work that I’m passionate about. It's truly fun! It all comes down to QUALITY and FREEDOM. If you’re in B2B SaaS and thinking about transitioning, fractional work lets you design a career on your own terms. 💡 Who’s ready to make the shift? 🏃‍♂️ DM me and let's talk. #FractionalWork #B2BSaaS #CareerFreedom #PreCallAI #EngineerMasterSolutions

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I was asked what is the fasted way to win new business for sales - get warm introductions in your target accounts. Here are 7 steps that I think will help you get radically more pipeline fast:🔥📈 Inboxes are overflowing, cold outreach is losing its punch. Warm introductions are the key to breaking through the noise and accelerating your sales pipeline. 1. Define Target Accounts 🎯 Zero in on accounts that align with your ideal customer profile. Know their challenges, and understand how your solution uniquely solves them. Focus on a subset you’re confident about – don’t let analysis paralysis slow you down. Key: Don’t get stuck on the first step; just go for it! 2. Identify Connectors in Your Network 🕸️ Expand your network (or automate this with platforms like https://lnkd.in/e-XsFVmR) to match up with contacts who have trusted relationships with key players in your target accounts. Look for people with deep industry and solution experience- they’ll help boost your credibility.  3. Engage with Value First 💬 When requesting an intro, lead with value. Show why the intro matters to their connection and how it benefits them. Remember, your Trusted Advisor isn’t your sales rep – they’re a facilitator of value for their network. Offer insights, unique perspectives, and collaborate in a knowledge exchange. This will set you apart as more than “just another sales rep.” 4. Personalize Your Outreach to the New Contact 🧑‍💼 After a warm into, skip the canned pitch. Reference your mutual connection, then tailor your message to your target accounts needs. Tap into your advisor’s inside knowledge on what truly matters, from active projects to key priorities. This approach makes you relevant, aware, and genuinely interesting. 5. Nurture the Relationship, Not Just the Opportunity 🤝 Warm intros open doors, but it’s the relationships that close deals. Focus on building trust, actively listening, and providing value. Even if there’s no immediate sale. 6. Don’t Forget Your Sales Process 🚀 Whether it’s Solution Selling, MEDDICC, or MEDDPICC, stick to your process to stay on track. Use your advisor’s insights to set you apart, but also to qualify out quickly – if it’s not a fit, pivot to protect your credibility and the trust of your connection. 7. Reward Your Trusted Advisor 🏆 Recognize your advisor’s role in your success! A thoughtful gesture, creative reward, or a few percentage points on the deal can make a significant impact. It shows appreciation, strengthens the partnership, and sets the stage for future collaboration. Warm introductions are your ticket to stronger connections, faster cycles, and higher close rates. Are you tapping into them? 🔑 And if you want to make this easy, check out https://lnkd.in/e-XsFVmR – the first platform designed to automate and scale your ability to find and leverage warm introductions into all of your target accounts. 🔗 #SalesTips #Sales #SDR #SalesPipeline #WarmIntroductions #ForceEquals

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AE: "Can you demo to this super warm prospect?" SE: "Sure, what top outcomes are they looking for?" AE: "Umm, here's the e-mail thread. Figure it out." SE: "We might need more information than this..." AE: "But we NEED the demo to sell it to them." SE: "Okay, when's the call scheduled for?" AE: "At 3pm. Today." SE: 😭😭😭 Can anyone relate? Let's change the narrative. #presalesevolution #solutions #sales

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Want to catch the WinsDay replay? Matt Calhoun and I chatted about... ➡ Pre-Sales Strategies ➡ Demand Gen: Avoiding Failure When Outsourcing ➡ First Go-to-Market: Pivoting Your Startup  ➡ SDR Success: Leaders' Role in Prospecting Some themes popped up.... ☑ being data driven ☑ getting your ICP right ☑ documenting your processes ☑ what does good like ☑ what clues does customer success tell us ☑ culture ☑ people first leadership ☑ know your worth (mindset) ☑ trust and candid conversations .....and so much more Check out the comments to catch the replay! #sales

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To date...Luster has prevented over 2,000 revenue impacting mistakes. By having the ability to measure AE, BDR, and CSM proficiency at the skill and behavior level, we can accurately predict and address the landmines that are about to rock your sales funnel. It's not simply about training. Its not simply about practice. It's not simple about coaching. It's about the ability to have a realtime, data driven read on your business, and the tools and capabilities to prescribe what's needed for success for every customer facing employee. Want to learn more about how Luster can be the crystal ball for your GTM team? Dance into my DMs!

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Salesloft is in the business of helping companies create durable revenue growth, which inevitably means helping companies scale. Far and away the most common misstep I see leaders make in the scale phase is a failure to scale process and planning alongside headcount and revenue projections. It’s an absolutely critical step for business longevity. Smaller companies have the benefit of agility, but as businesses grow, it becomes increasingly difficult to make adjustments on the fly. It’s like steering a big ship – it just turns slowly. Adjusting to this new timeline can be difficult, especially for companies that have scaled quickly and within a different market dynamic than what we face today. They need to take a page from the book of their publicly owned peers and set goals for 6 or more quarters out, then work backwards to identify what needs to happen today. Every choice you make must be framed around the question, “Is this the most important body of work for our customer base, our ability to scale, and our ability to differentiate and win?” This also extends to software investments and digital transformation planning. Companies that intend to scale need to evaluate the platforms they’re considering through the lens of 2-5 years. That means making sure the option you choose not only solves the problem you face right now but can grow and adapt as your business evolves. Platform investments need to drive speed of execution, mitigate risk, and provide innovation that increases the return on investment in the future years. If you don’t trust your vendor to outpace your growth with their own innovations – or help you anticipate the challenges that will come with growth and prepare for the methodical turn toward them – then it’s not the right choice. Keep that in mind as you optimize your growth and investment strategy. #salestech #revtech #B2Btech #revenueorchestration

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🚨 Brag alert: If you've attended one of our Adobe Express for Edu trainings in Utah, chances are... you've had the opportunity to work with Zachary Ordoñez, who is undeniably one of my favorite people I've had the opportunity to partner with since starting at Adobe. 💪 Zach is known as someone who will take a training from "professional development" to "a creative PD experience." He's known for his dad jokes, his "swag bars," his innovative approaches to weaving creativity into student work, and-- most importantly, his deep understanding of teachers, students, and Adobe Express. As the brilliant school counselor I worked with at my old school always said, "If you see something you appreciate, SAY IT. Compliments make people feel good, and they make you feel good too." So-- Zach, you are awesome! 👍 If you need to give a shout out to someone who you appreciate, do it!! (Silly AI picture of Zach & I featured below)

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Yesterday, I talked about how we bucketed lead sources to ensure we were spending our dollars on the right channels and targeting the right people. Once we had that figured out, we moved to the next critical piece: Nurturing every lead. Because let’s face it, leads don’t convert on the first touch. To move leads through the funnel, we needed an airtight system to keep them engaged and guide them to the next step. Here’s exactly what we built: 1️⃣ After our Lead Form Was Filled Out: Once a form was submitted, automation kicked in immediately to create trust and keep the lead warm: Social Proof Texts + Emails: Stories of satisfied customers and raving fan testimonials helped build confidence. Even early on we would send our one happy customer 😂 What to Expect: Clear, automated texts outlined the process ahead to set expectations. 2️⃣ After the Appointment Was Booked: Once a lead booked an appointment, the goal was simple: ensure they showed up. Reminders: Emails and texts sent 24 hours and 1 hour before the appointment to reduce no shows. Prep Guides: Quick tips to help them feel ready and comfortable for the consultation. Value Reinforcement: Messaging that reinforced the benefits of working with us kept excitement high. 3️⃣ If They Canceled or Didn’t Show: No shows and cancellations happen, but we didn’t let those leads go. They already said yes to a meeting, after all: Reschedule Prompts: Automated emails made it easy to rebook at their convenience. No show and cancel sequences: Texts that continued to reinforce the cost of inaction + how working with us would benefit them. 4️⃣ After They Closed but Before Install: Once a customer signed, we still had work to do: Install Prep Sequences: Step by step emails explained what to expect on install day. Countdown Emails: Reminders leading up to the big day kept them engaged and excited. Social Proof Round 2: More testimonials reminded them they made the right choice. 5️⃣ After the Project Was Complete: Even after the job was done, our automations kept working: Referral Requests: Simple, incentivized referral programs turned happy customers into promoters. We call them Ambassadors now and they can earn $1000 for every customer they bring to us that installs. Feedback Surveys: Follow ups to gather feedback. This happened post sale, post install and a few months later. Our CSAT and NPS drove a lot of our operational decision making. Upsell Campaigns: Maintenance plans and add-ons were introduced strategically to maximize lifetime value if they weren’t sold at first meeting. The result? This nurturing system ensured no lead was forgotten and every customer stayed informed, engaged, and excited, whether they converted in one week or six months. Monday, I’ll share Step 3 of the RevEngine: Sales Scripting, Enablement, and Strategy. Because the key to scaling isn't about getting MORE leads, it's about setting up your sales reps for massive success.

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I see posts about "sales funnels" several times a day by RevOps and sales "leaders." It drives me insane. 🤬 Rant below. Almost every single piece of report, audit, or market study will tell you that buyers do not buy in a funnel. Sales funnels have been debunked at least 6,000 times, yet it's ultimately what sales and RevOps leaders implement to "track" revenue. It feels a bit like the '50s when advertisers were promoting the health benefits of cigarettes, like stress relief, weight control, and even better lung function: "More doctors smoke Camels" and "Reach for a Lucky instead of a sweet." Sales funnels don't kill people, but they certainly kill careers.

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