Cassie Young’s Post

Fighting tough battles ( I mean every large deal) in tech sales can take months, even years. But winning? That gives you a rush like no other. It's addictive. You're not satisfied with 100% anymore. You want more. I've been there. I got hooked too for years. Now, I chase a different high. It's the thrill of watching the heartbeats of any tech company, the sales professionals transform. My role is simple. Work on the mind shifts. Leverage Rituals, Processes, Tools and Build Systems. Get them hungry, find direction and start following simple, effective tactics. It takes only a few months to start seeing the results. In one of the recent assignments... Our goal: Set the rituals and elevate X's sales managerial skills. He was managing his team with limited structure. Some success, but major struggles. Priorities were unclear. No system for managing the sales funnel. Tracking and analysis needed serious improvement. We tackled these issues head-on. In just a few weeks, efforts started showing movements. X started learning the art of tracking > (only) 3 key KPIs. We implemented a simple, powerful tracking system. The results? Improved Results ~ +35%. New team alignment emerged. Sales processes improved dramatically. All this, in the first 3 months. He just needed practical, battle-tested strategies and direction. We delivered exactly that. Critical priorities? Established. Effective sales funnel management? Developed. Simple yet powerful tracking methods? Implemented. Sales rituals? Followed. X empowered his entire sales team with new strategies. He started planning for the upcoming quarters systematically. The team started gaining new confidence when failure was not an embarrassing event but an opportunity to grow. New GTMs were continuously applied and adapted. The team is filled with a fresh sense of accountability to produce results. This is why I get pumped. Working with leaders like X who act RELENTLESSLY. Who are committed to elevating their teams. Now, we are adding one more arsenal to their GTM - https://techsalesos.com. EMpowering the CORe is COREM.

🌟 Spotlight 🌟 Meet Michael Schwab—a good friend of mine and one heck of a sales leader! He could use our help finding the next awesome role. Mike is a skilled sales leader with over a decade of experience at top tech companies like Google, Amazon Web Services (AWS), and Oracle, known for consistently exceeding sales targets, building partner ecosystems, and closing high-value deals. He excels in developing go-to-market strategies, fostering partnerships, and driving revenue growth across diverse regions. 🙏 How you can help: If you know of any opportunities or can connect Mike with someone who does, feel free to reach out to her directly, or DM me. Your introductions, connection requests, reposts, and likes/comments are greatly appreciated! 🙋♂️ More on Mike: - Looking for a Regional Sales Manager position, Account Executive, Territory Manager, etc. - Based in DFW, Texas - Prefer Remote - Open to travel, but the less the better - Industry: K12 education, but open to new industries - Passionate about: He loves to cook! The kitchen is his happy place! - Something Unique: He was on the Weber Grills homepage for a contest he won. 🛠 Relevant Experience: - Sales Leadership: Over a decade of experience in sales, account management, and business development, with roles at top tech companies like Google, AWS, Dropbox, Oracle, and Amazon Web Services. - Regional Management: Managed territories across multiple states and regions (Texas, California, U.S. West Coast, and Canada) and developed go-to-market strategies to drive sales growth. - Channel and Partnership Development: Built and scaled partner ecosystems, transitioned from direct to reseller models, and developed strategic partnerships to support sales initiatives. 🏆 Achievements/Results: - Revenue Generation: Consistently exceeded sales targets, including $1M+ in ARR at ParentSquare, 102% revenue attainment at AWS in 2020, and 109% quota attainment at Google for Work. - Business Development: Led successful market entry strategies for AWS and Google, significantly growing pipelines and establishing new revenue channels. - Account Management: Closed large enterprise deals with key clients, including GARLAND ISD, Georgetown ISD, Staples, PepsiCo, and numerous school districts, driving significant revenue growth. 💼 Professionalism: - Cross-Functional Collaboration: Experienced in working with diverse internal teams and external partners to develop and implement sales strategies and solutions. - Thought Leadership: Conducted executive briefings, symposia, and workshops, and provided industry expertise at large conferences and events. - Mentorship and Team Development: Recognized for mentoring and training sales teams, developing territory strategies, and fostering growth within organizations. #Sales #SalesLeadership #AccountExecutive #Leadership

My biggest mistake as a first time VP Sales? Not understanding which team I was on. Let me explain: I focused a lot of time on the sales team, my direct reports. I helped build the sales process from the ground up. I hired, onboarding, trained, coached, and promoted reps. I watched pretty much every intro call. I coached deals. I built dashboards to help me focus on fixing problems within the sales team. That was 90% of what I was doing. But there was other work to do. With my first team: the exec team. See, as a VP Sales, your team is the rest of the execs. Your job as executives is to set the strategy, vision, and direction with the rest of the VPs. Then as a team of VPs, you go out and execute on the strategy. You all make hires, changes to processes, allocate resources, make cuts, etc. In order for the company to fulfil on the strategy. And I didn't realize until after I was done as the VP Sales, and reflected on my time, that this was the team I needed to align with the most. We were going up-market. Which meant there needed to be product changes, changes in marketing/positioning/targeting, changes in how we serviced the customer. If the exec team isn't fully aligned with the changes that need to happen to execute on a strategy (like going up market), then every team will fail to some extent. So as a VP Sales, your direct reports are very important. They're executing on the sales part of the strategy. That's your responsibility to make sure execution is flawless. But aligning on the strategy, and making sure that every team is executing? That's the real focus of a VP. Your team are the other VPs. Once you realize this, you can make significant progress as a company. If nobody on the exec team realizes this? It becomes a mess.

“As my career evolved into enterprise sales, I maintained my commitment to learning the intricacies of clients’ businesses, products and buyer journeys. This ability to absorb vast, highly-complex information and distill it into clear, impactful insights has become my superpower as an enterprise seller.” — Sara Oberst, VP of Growth at Bounteous x Accolite Enterprise sales is its own beast! Built In Chicago found two sales leaders to share their insights on how to break into enterprise sales and strategies to make it stick. Read the story here: #salesjobs #techjobs #nowhiring

Sales Dev: Report to marketing or sales? It's the age-old question. 💡 Exciting changes this week at Lattice, as the SBDR team reporting lines shifted from Marketing to Sales. Reflecting on this switch, here's my thinking: 1. There's no one-size-fits-all when it comes to where Sales Dev should report. As Sarah Franklin wisely shared this week, the key is finding the org structure that works perfectly for your company and your goals. 2. While initially aligned with marketing at Lattice, the move to Sales doesn't weaken our partnerships. GTM alignment at the top of the funnel remains crucial. Collaborating with marketing partners has been invaluable in driving strong programs and growth. We won't be slowing this down - Rachel Sadacca and our DG/MOPS team couldn't get rid of me, even if they wanted to 😉 3. I've been asked throughout my career if I have a preference for sitting under sales or marketing - the truth? I really don't. The most important asset for Sales Dev leaders is having leadership that understands the value of the function and supportive cross-functional partners. I am extremely grateful for the incredible support and shared vision with our CMO Elizabeth Walton Egan that brought me to Lattice. But the vision has also always been shared with our sales and revops leaders through close collaboration in order to enhance the impact of pipeline generation efforts. This shift brings minimal day-to-day changes - in the best possible way! Our focus remains on strengthening pipeline generation efforts and talent development. 🏋♀️ Excited to continue elevating this function under the leadership of Tessa del Rio. The journey continues, and we're just scratching the surface. Which camp do you sit in - Sales Dev reporting to marketing or sales?

If you're in sales, here's how to save yourself a decade of pain. The first decade of my career looked like this: - Age 22: College dropout as a socially anxious introvert - Age 26: Constantly hustled (day job as an Account Manager and a 2nd job at night as a DJ just to pay the rent in NYC) - Age 28: Filed for bankruptcy - Age 32: Landed in the hospital with a mini-stroke I was constantly reacting to my circumstances and then grinding away to play catch up. Over time, however, I slowly learned to unsubscribe from the hustle culture that was so pervasive in SaaS sales (you know, the “rise and grind” mentality) and adopted a more human-centered approach to my work. At the heart of it was embracing design thinking, which helped me make more purposeful decisions and connect the dots between my long-term ambitions and the small actions I needed to take each day. And what an impact it made in the 2nd half of my corporate sales career: - Age 38: Paid off my house in full - Age 39: Reached the 7-figure earners club for the first time (and repeated 3x in a row) - Age 41: Able to purchase a 2nd place in downtown Chicago - Age 42: Retired from the corporate world to become a digital creator Today, I stay connected to the “frontlines” by working closely with a handful of enterprise and strategic tech sellers. Sadly, through their experiences, I haven’t seen much improvement in sales environments over the past few years. In fact, in many ways, the industry is moving in the wrong direction. I’ve been vocal on LinkedIn about these issues facing most strategic SaaS sales teams today, but unfortunately, a lot of leaders refuse to let go of their tight grip on operating the “old way.” My observations have concluded that this is based on 3 main culprits: 1/ FEAR. Constant pressure from the top doesn’t allow leaders to experiment with alternative approaches. 2/ DATA. ”Activity” metrics are easier to measure and create incentives around than “impact” metrics (which require a bit more patience and going deeper with prospects and customers). 3/ OVERWHELM. A lot of leaders are simply ill-equipped to manage high-performance teams and revert to old ways of thinking when there’s simply too much on their plate. Design thinking, however, puts the human at the center of everything (whether it is the customer or the individual seller), and it improves the experience in every regard. It’s the basis for developing a strong personal operating system. I share this better way here: https://buff.ly/3R6dus1 🐝 P.S. Be sure to subscribe while you’re there and new tips drop every Wednesday morning.

Krysten Conner shares a GREAT post that I wish my early 20s self had known. It forces a seller to do a few things. 1. Rigorously (dis)qualify a deal! It will make you qualify a deal deeper, which is always a good thing. 2. Features only matter because of the results they drive. Focus on that. 3. The "Why anything" and "Why now" question - helps us a seller determine how impactful the project is, and will help the seller prioritize their time...(and respect the customer better). 4. Always, have metrics, or a compelling story involved. The more your deal costs, the better the numbers and story have to be. Hope this helps others, strongly recommend any salesperson follow her (Along with Jen Allen-Knuth + Kyle Asay; all 3 have awesome tips.)

𝐓𝐫𝐚𝐧𝐬𝐢𝐭𝐢𝐨𝐧𝐢𝐧𝐠 𝐟𝐫𝐨𝐦 𝐅𝐨𝐮𝐧𝐝𝐞𝐫-𝐋𝐞𝐝 𝐒𝐚𝐥𝐞𝐬 to 𝐅𝐨𝐮𝐧𝐝𝐞𝐫-𝐌𝐚𝐧𝐚𝐠𝐞𝐝 𝐒𝐚𝐥𝐞𝐬 The best early-stage founders are also the best salespeople —no one knows the product better or has more passion. But as your business scales, so must your approach to sales. That’s where the shift from founder-led sales to founder-managed sales becomes essential. Here are some important points: 📈 𝐓𝐡𝐞 4 𝐒𝐭𝐚𝐠𝐞𝐬 𝐨𝐟 𝐒𝐚𝐥𝐞𝐬 𝐆𝐫𝐨𝐰𝐭𝐡: - Founder-Led Sales (up to $1M ARR): You’re doing all the selling to early adopters, often within your network. - Transition Phase ($1M to $3M ARR): You begin hiring your first sales hires or a VP of Sales and shift to managing the sales process rather than closing deals yourself. - Managed Sales ($3M to $10M ARR): A sales leader drives the strategy while you oversee from a higher level. - Scaling Sales (Above $10M ARR): You’re building a repeatable and predictable process with account execs, SDRs, and customer success teams. 𝐁𝐮𝐢𝐥𝐝𝐢𝐧𝐠 𝐭𝐡𝐞 𝐑𝐢𝐠𝐡𝐭 𝐒𝐚𝐥𝐞𝐬 𝐅𝐫𝐚𝐦𝐞𝐰𝐨𝐫𝐤 𝐛𝐞𝐟𝐨𝐫𝐞 𝐛𝐫𝐢𝐧𝐠𝐢𝐧𝐠 𝐨𝐧 𝐚 𝐬𝐚𝐥𝐞𝐬 𝐥𝐞𝐚𝐝𝐞𝐫 𝐢𝐬 𝐧𝐨𝐧-𝐧𝐞𝐠𝐨𝐭𝐢𝐚𝐛𝐥𝐞. 𝐇𝐞𝐫𝐞'𝐬 𝐡𝐨𝐰: - Define your ICP (Ideal Client Profile): Start narrow, identifying your Minimally Viable Customer (MVC) before expanding. - Nail Pipeline Management: Focus on quality leads—tighten your MQL (Marketing Qualified Lead) to SQL (Sales Qualified Lead) conversions and build repeatable outbound messaging. - Optimize Partnerships: It's easier to grow revenue with existing customers than acquiring new ones—prioritize reducing churn and expanding your share of wallet. 🔥 𝐊𝐞𝐲 𝐈𝐧𝐬𝐢𝐠𝐡𝐭𝐬 𝐟𝐨𝐫 𝐅𝐨𝐮𝐧𝐝𝐞𝐫𝐬: - Do the Groundwork: Build your sales framework before hiring a head of sales. This ensures the foundation is strong and scalable, setting up your future team for success. - Be Ready for the Hard Questions: Building a framework forces you to address difficult decisions about your market, sales strategy, and customer base. If you're an early-stage founder scaling up, don't wait to build out this structure. It can make all the difference as you grow beyond your network and into a repeatable, predictable, and scalable sales process. Read more from sales leader Brett Orlanski, on how to master the transition: https://lnkd.in/g7mziwhn #StartupGrowth #SalesLeadership #FounderTips #SaaS #RevenueGrowth #SalesFramework

You have just been hired as the new national sales manager for a company that has experienced a plateau in sales or is not hitting the number. You are getting to know the issues to be addressed in the business, and your CEO is hastily waiting for the new sales initiatives to be implemented to deliver revenue growth. They need to realise an increase in sales and effective sales reps. What do you prioritise that will impact the business in the short term and also play the long game for the company? #salesmanagement #salesteam #salesforce #salesleadership #CEOTips #salesgrowth #businessgrowth