Time Management for Sales Reps

I got Outreach to its first $2M selling booth-to-booth at conferences. I did the exact same thing at my new company Paid. Here's my playbook for selling at events (without spending $50k on a booth): Selling booth to booth at conferences is the ultimate founder hack. It's like going to a bazaar where you're both a buyer and seller. It's energizing! And it's the highest ROI marketing and sales activity for early-stage companies. Here's the playbook: 1. Have a plan Have a target list of at least 10 qualified prospects ready before the event. Study the map of the event. Find your top targets. Make a walking route. Make a list of the follow-up meetings you are going to be walking away with. The night before, visualize yourself nailing those conversations. 2. Recon walk Before you do anything, take a walk along the whole conference space. You will get a vibe for who is there. What booths brought in senior leaders. Which one is just junior sellers. Which ones to avoid. Where the good free food and drinks are. 3. Stay fed and hydrated Working the conference floor is like going to Disneyland. The experience is so much more enjoyable if you know where the churro carts are. Stay hydrated and figure out how to get to food quick. Pitching consumes a lot of brain power which uses sugar as fuel. Make sure you are snacking and drinking constantly, especially the good stuff. 4. Nail the timing If you are selling to rank-and-file, driving awareness, or gathering info on a prospect, wait for the keynote speakers to go on before you make your move. Anyone who is not a boss is left behind manning the booth with nothing to do while their bosses go to the main stage. Prime hunting time! If you are selling to executives wait for the happy hour. They are relaxed, their guard is down. This is the easiest way to book follow up meetings. 5. The sale Approach the booth like a buyer. Always start curious and ask about their product. Get the full pitch. Use this as discovery. Ask thoughtful questions, be engaging. When the rep asks you about what you do, then you launch into your pitch and make your ask. Reps are always looking to help another, figure out a way to help that rep too. Reciprocity works. 6. Do one more rep Winners are winners because they practice more than the rest. When you are tired and ready to leave, do one more booth. That last sale will surprise you. At this time, even if you feel tired, you are so dialed that the last few will be your best ones. 7. Practice Practice Practice Selling at conferences is a sport. Practice will make perfect here. Go to SaaStr, go to Inbound, go to smaller venues to prepare for Dreamforce, RSA and AWS reinvent. Save the booth for when you're $10m+. Eventually you get big enough that you have to, but early on as a founder you just buy the lowest price tickets and sell as much. I spent $2,000 on tickets my first conference season at Outreach and got $2M back. Not a bad ROI.

How I saved a tech company $128,557 in 22 days (without hiring more staff): $128,557. Gone. All because they didn’t trust their CRM to do its job. Here’s the story: - 185 employees - A growing tech company - Held back by CRM inefficiencies Their marketing director was wasting 5.5 hours a day on low-level tasks: Manually entering lead data into three CRMs: - HubSpot - Google Sheets - Salesforce The result? - Typos and bad data - Gut-feeling decisions - Delayed reporting Let’s crunch the numbers: 110 hours a month—lost. 165 working days a year—wasted. A staggering $128,557—down the drain. Here’s how we fixed it: First, discovery. We identified every inefficiency and bottleneck. Then, build. We integrated HubSpot with Salesforce and eliminated Google Sheets. Finally, testing. Everything was run in Salesforce Sandbox, approved, and launched. 22 days later, their system ran like clockwork. The result? 110 hours saved every month $128,557 in yearly costs eliminated And their marketing director? Back to focusing on real high-level work. P.S. What’s one inefficiency that’s holding your business back right now?

I used to think hustle was the key to high performance. Then I learned the real secret: REST is the most powerful RGA. Most sellers grind themselves into dust chasing performance. But I’ve coached 100s of top performers—and the highest earners don’t work more hours. They master their energy. Here’s how I worked 40 hours a week (never work nights or weekends) and still outperformed 99% of reps: Let’s flip the script on what it takes to be a top performer in sales. Everyone talks about RGAs—Revenue Generating Activities. But no one talks about the energy required to do RGAs well. If you want to prospect with intensity, sell with presence, and close big deals— You need rest. At a mastermind recently, someone called it the “Ultimate RGA”: Rest Generating Activities. Because without rest, RGAs fall apart. You’ll be foggy. Reactive. Distracted. You’ll confuse activity with impact. Here’s how I train reps to recharge intentionally—so they can win without burnout: 1. Plan 4 Vacations a Year I pre-block 4 weeks off annually. They’re non-negotiable. It doesn’t matter if it’s Hawaii or your local mountain trail— The key is knowing you are unavailable. Not half-working. Not checking Slack. Fully present. Fully off. 2. Track and Protect Your Sleep I use a WHOOP. You can use anything. But if you're not sleeping 7+ hours, consistently, you’re underperforming. You can’t bring intensity to your calls when you’re running on fumes. Sleep is a performance multiplier. 3. Calendar Block Your Breaks My calendar is blocked 12–1 PM every day. Lunch with my wife. A walk. Or just quiet. Three hours of deep work → 1 hour of recovery → back for the final sprint. Burnout doesn’t happen from work. It happens from nonstop work. 4. Ruthless Time Boundaries I stop work at 5 PM most days. No nights. No weekends. Ever. You don’t need 70 hours a week to crush quota. You need to stop saying yes to distractions and start owning your schedule. Parkinson’s Law is real: The less time you give yourself, the more efficient you become. 5. Say No to Busy Work I use the 12 Week Year system. Everything I do ties back to a goal. Internal meetings? Minimized. Slack and email? Batched and time-boxed. If it doesn’t move pipeline or drive impact, I don’t touch it. If you’re working 60+ hours and still missing quota... It’s not your work ethic that’s broken. It’s your calendar. Stop measuring your week by hours worked. Start measuring it by energy invested in what matters. You don’t need to grind harder. You need to recharge better. Work less. Sell more. Live fully.

The number one reason top sales reps burn out isn't quota pressure. It's because they work incredibly hard at their job but completely neglect working hard on themselves. Here's what I discovered managing a $195M sales organization: The reps who lasted and thrived weren't the ones grinding 12-hour days in their CRM. They were the ones who built systematic approaches to their entire life. Sales is a game of habits, not just hustle. When you only focus on quota, you're building a house on sand. When you work on yourself systematically, everything improves. The top performers I mentored used what I call the four-part productivity system: #1 The PACER Calendar Method. They color-coded their calendars into five buckets: Personal (purple), Admin/Action (red), Creation (deep work), Enrichment (learning), and Recovery (yellow). This prevented them from being reactive to whatever hit their inbox. #2 12-Week Planning. Instead of annual goals, they broke everything into 12-week sprints with clear micro-steps. They knew exactly what to focus on each week to hit their biggest goals. #3 Daily Win System. Every night, they spent 5 minutes journaling three wins, decisions made, and lessons learned. This prevented the "what did I even accomplish?" spiral that kills motivation. #4 Weekly Reset Protocol. Every Friday, they did a 30-60 minute review of energy vs. time, cleared their workspace, and planned the next week intentionally. When they did these, they showed up with more energy, clearer thinking, and better resilience. Your prospects can feel the difference between someone operating from burnout versus someone operating from a place of systematic strength. Stop treating personal development like it's separate from sales performance. When you become a better version of yourself systematically, everyone benefits. Your family, your team, your prospects, your bank account. — Want to build an ELITE routine and mindset? Watch this: https://lnkd.in/gbpFye_t

The hardest part of being a salesperson? Not closing deals? Not handling objections? It’s updating the CRM 😅 We’ve all been there. But your CRM is only as good as the data you put into it. If it feels like a chore, it’s time to make it work for your team, not against them. Here’s how: 1️⃣ Simplify the process Too many fields or unnecessary steps? Cut them. Keep it lean so your team can focus on selling, not admin work. 2️⃣ Automate data entry Use tools like email tracking, call logging, and activity sync to handle the basics. Less manual input = happier reps. 3️⃣ Make it useful for reps If your CRM feels like it’s only for managers, no one will care. Show reps how it helps them prioritise leads, track follow-ups, and close more deals. 4️⃣ Provide proper training Don’t assume everyone knows how to use the CRM effectively. Run training sessions to show shortcuts, best practices, and how it fits into their workflow. 5️⃣ Reward good habits Recognise and reward the reps who consistently keep the CRM updated. Positive reinforcement goes a long way. 6️⃣ Use data to sell smarter Make the insights visible and actionable. Show your team how CRM data can uncover trends, highlight hot leads, and predict customer needs. 7️⃣ Integrate CRM with other tools Make it seamless. Connect your CRM to email, calendars, and project management tools to reduce context switching and manual effort. 8️⃣ Set the tone from leadership If managers aren’t updating the CRM, reps won’t either. Lead by example and make it part of the team’s culture. 9️⃣ Limit duplicate data entry Nothing frustrates a salesperson more than entering the same information in multiple places. Streamline your systems to avoid redundancy. 1️⃣0️⃣ Review and refine regularly Your CRM setup isn’t set in stone. Get feedback from your team and adjust workflows, fields, and tools to make it more effective over time. Updating the CRM doesn’t have to be the hardest part of the job. A few tweaks can turn it into a tool your sales team wants to use. What’s your team’s biggest CRM challenge and how have you solved it?

Conference fatigue is real! Attending conferences can be rewarding and energizing, but the packed schedules, travel, information overload, and constant networking can quickly lead to fatigue or even burnout. Here’s a few ways to stay refreshed, focused, and make the most of your conference experience: ➡️ PLAN AND PRIORITIZE YOUR SCHEDULE: -- Review the agenda in advance. Highlight the sessions, speakers, and events that align with your goals. Focus on quality over quantity and don’t feel pressured to attend everything. -- If you’re traveling across time zones, use jet lag apps like Timeshifter or StopJetLag to help your body adjust. These apps provide personalized plans to optimize sleep, light exposure, and meals, which can significantly reduce. -- Schedule intentional downtime. Block out periods for solo walks, quiet meals, or short breaks in your room to recharge. Over-scheduling is a major contributor to event fatigue. -- Build in transition time between sessions. Even five to ten minutes can help you reset and prepare for the next event. ➡️ PREPARE FOR NETWORKING AND MEETINGS: -- Carry old-school business cards and a pen. -- Have your LinkedIn QR code or a digital business card ready for quick sharing. Digital cards (using apps like HiHello, Inc. or Popl) are increasingly popular. -- Download the conference app if one is available. They often include networking features, schedules, and ways to connect with other attendees efficiently. ➡️ DURING THE CONFERENCE: -- Limit distractions and avoid multitasking during sessions, meetings, or conversations. -- Be intentional and selective with your #networking: Focus on meaningful connections rather than collecting as many business cards as possible. -- Take notes during or immediately after key conversations and sessions. This helps you remember details and makes follow-up easier. -- Listen actively and ask thoughtful questions-engaged participation is more valuable than passive attendance. -- Designate some “no-conference” time: Block out periods where you don’t attend any sessions or meetings to decompress. -- Skip non-essential social events (like early breakfasts or late-night mixers) if you need rest. Prioritize your well-being over FOMO. -- Pay attention to your body and mind. If you feel overwhelmed or exhausted, take a break, even a short one can help you reset. ➡️ SCHEDULE TIME FOR FOLLOW-UP: -- Review your notes and contacts as soon as possible after the event to combat the “forgetting curve”. -- Set calendar reminders to follow up with new connections-ideally within a month, and then periodically (such as quarterly) to maintain relationships. -- Send personalized LinkedIn connection requests to everyone you met, referencing your conversation to reinforce the connection. -- Use #technology to your advantage: AI-powered apps can help summarize sessions, organize notes, and remind you of action items. What’s your best tip to avoid conference fatigue❓

AI in Sales—Augment, Don’t Replace! 🚀 AI won’t replace salespeople. But salespeople who use AI strategically will outperform those who don’t. I’ve been in sales since Girl Scout cookies were 50 cents a box, and I’ve seen the game change. But nothing has been more transformative than AI. According to LinkedIn for Sales Connect monthly newsletter, AI can reclaim 29% of a rep’s time by automating admin tasks, data collection, and customer insights. The key? Using AI to amplify human strengths, not replace them. Yet, there’s a challenge: 60% of sales teams report being overwhelmed by the sheer volume of administrative work.AI can help offload up to 10 hours of non-selling tasks per week, effectively doubling selling time from 10 to 20 hours. That’s the kind of efficiency shift that drives real revenue. Here’s how to strategically automate without losing the personal touch: ✅ AI-Powered CRM: Let AI handle lead scoring, email follow-ups, and data entry so reps can focus on relationship-building. ✅ Smart Workflows: Use AI tools to automate routine tasks, freeing up time for strategic selling. ✅ AI as a Guide: Train your team to use AI-generated insights as a tool, not a crutch. Judgment and creativity still win deals! 📌 Actionable Step: Identify 3 repetitive tasks in your sales process (CRM updates, lead research, follow-ups) and integrate AI-powered automation. Measure the time saved and reallocate it to higher-value selling activities. AI isn’t the future of sales—it’s happening NOW. How is your team leveraging it? Let’s talk in the comments! #AIinSales #SalesLeadership   #WomenInSales #EnterpriseSales #1MillionWomenby2030 

There’s a myth in sales that if you just worked harder, you’d close more deals. Wake up at 4 AM. Hammer out 100 more cold calls. Work late. Work weekends. Grind until you “make it.” Except… that’s not actually how it works. If working more equaled selling more, every rep who pulled 80-hour weeks would be a millionaire. They’re not. Why? Because sales is about leverage, not effort. Here’s what actually works: Quality over quantity. 20 well-researched, well-written cold emails will always beat 200 generic ones. Stop doing busywork that doesn’t move the needle. Deep work beats long hours. Three hours of focused prospecting is more valuable than a 12-hour day filled with Slack messages, LinkedIn scrolling, and “quick check-ins.” Know when to log off. If you’re staring at your CRM at 8 PM, re-reading the same deal notes for the 10th time, you’re not grinding—you’re wasting time. Shut the laptop. Take a break. Sales isn’t about who works the most hours. It’s about who works the smartest. The top reps aren’t the ones who burn themselves out. They’re the ones who use their time intentionally, focus on high-value activities, and protect their energy so they can keep selling long-term. Hustle culture is a scam. Be strategic. Be efficient. And for the love of all things good—log off once in a while.

Your sales manager is never going to ask you if you updated the CRM again. That sounds like a small win. But it's not. HubSpot just shipped Smart Deal Progression — and it solves one of the most persistent, quietly relationship-straining problems in sales: the gap between what happened on a call and what actually gets logged. Here's what it does after every customer call: 1. Reads the full meeting transcript 2. Cross-references your deal history — emails, notes, prior activity, timeline 3. Surfaces suggested CRM updates: deal stage, close date, next step, outcome 4. Drafts the follow-up email 5. Flags action items while context is still fresh You review and confirm. Then move on. This isn't AI generating generic next steps. It's your CRM doing the reasoning — using your pipeline definitions, your deal stages, your team's actual workflow. Why it matters in regulated accounts: In financial services and healthcare, the audit trail isn't optional. Every touchpoint needs to be documented and accurate. Smart Deal Progression doesn't just save time — it raises the floor on visibility across every active deal. For any AE managing 15+ active accounts: the question isn't whether you'll miss an update. It's how fast you catch it. Now it catches itself.

Sales broke me at least three times. But each time taught me something critical about survival in this game. The highest highs followed by crushing lows. Deals you worked on for months slipping away in the final hour. Watching colleagues celebrate while you're stuck explaining another loss to your manager. Then Q1 hits. Back to zero. Every single time. Your mental health becomes collateral damage if you're not careful. I learned this the hard way watching talented reps burn out completely. Some never came back to sales. Here's what keeps me grounded through the chaos: • Separate your identity from your results. You are not your quota performance. • Build routines outside work that recharge you. Exercise, hobbies, relationships that matter. • Remember that every deal teaches you something valuable, even the ones that fall through. The emotional rollercoaster never stops in sales. But you can learn to ride it instead of letting it ride you. Your future self will thank you for protecting what matters most. Take care of your mind. Everything else depends on it.