Destry Roberts’ Post

I’ve been doing outbound sales my entire sales career. Most of the time I’ve been opening green field markets. Meaning doing outreach to the unknown. And it can be brutal. I’ve had zero sales months, sometimes multiple in a row. I’ve led teams who’ve been on the brink of losing faith and hope. I’ve missed targets, budgets and expectations. I’ve had sleepless nights trying to figure out how to make things work when nothing seems to be working. At least that is what outbound looks like on the surface, short-term. It takes 12-18 months to close outbound deals on average. In your home market the sales cycle can be less than 6 months but the further away you sway from the homebase, the longer it will take. Add representing an unknown brand into the picture, the sales cycle extends even longer. The final component to the equation is not selling in the local language, and we’re close to 24 months. Faith is not a strategy, we’ve all heard that. But in outbound sales it’s what keeps you going, in the long run. Faith that sticking to the process will bring results, faith that repetition and being relentless will pay off. And data backs this up as well, so it’s not just based on my gut feeling. Same as with sports: the more you train the better you become and the more you play, the likelihood of winning a game will increase. Why outbound sales you might think. Well, I always say it’s for the crazy ones. What makes it worth it after all is said and done is the taste of victory. There’s nothing quite like the feeling than accomplishing something that you thought you couldn’t.

The new end-to-end sales rep: Why the industry needs a wake-up call (...and how to avoid getting left behind): The sales industry is getting a bad rep. Why? Too many reps are like French Bulldogs: ❌ Lazy ❌ Soft ❌ Complaining constantly ❌ More focused on comfort than results This "laptop lifestyle" mentality is killing businesses. 4 inbound calls, off at 2 PM, sipping margaritas? That's not sales. That's vacation. The new end-to-end sales rep? They're Belgian Malinois: ✅ Hungry for work ✅ Relentless ✅ Will climb a 30-foot wall just because you asked ✅ Goes to the end of the earth to close deals High-level business owners are waking up. They see that 90% of sales reps are: • Lazy • Untalented • Can't follow up • Leave prospects at one touch point • Won't go the extra mile The industry is changing. The hungry will devour the complacent. Which one are you? If you're not a "work dog," it's time to change. This is your wake-up call. Be the rep that owners fight to keep, not the one they can't wait to replace. - PS, Ready to become an unstoppable end-to-end sales rep? Upload your profile to Closify and land your next high-commission job in as little as 7 days. DM 'Sales' to get started.

Life in B2B sales... [brutal, I tell you🤣 🕊️ ] Sales rep: First, we connect on LinkedIn. Then, I spend three weeks liking their posts and commenting on industry news. Manager: Good, good. And then? Sales rep: Then I send a carefully crafted email, wait two days, and follow up with a voicemail. Manager: And then? Sales rep: We finally get a meeting! I listen intently, build rapport, and customise our proposal for their exact needs. Manager: Impressive! And then? Sales rep: They tell me they’re thrilled but... “not ready to commit.” So, we agree to reconnect next quarter. Manager: And then? Sales rep: … And then I find them signing with our competitor. Manager: Ah yes, the circle of sales.

Inside Sales: A Job or an Art? Let’s be honest—inside sales can feel overwhelming at times. The pressure to hit dialled call quotas, the repetitive pitching, and the constant scrutiny can sometimes make us feel like machines, churning out calls without purpose. But here’s the truth: inside sales isn’t just about numbers or pitches—it’s about people. When you shift your perspective, it transforms into something much more fulfilling. Inside sales becomes the art of building trust and meaningful relationships. It’s not about pushing products or closing deals through clever tactics; it’s about genuinely understanding your client’s needs and guiding them toward solutions that add real value. Trust is the key, and it’s earned when you truly believe in what you’re selling. The stronger your conviction in your product, the easier it becomes to inspire that confidence in your clients. At its heart, inside sales is about being authentic, empathetic, and human. It’s about listening actively, communicating clearly, and connecting deeply. So, the next time you pick up the phone, remember—you’re not just making a call; you’re creating an opportunity to build trust, solve problems, and make a difference. Sales isn’t just a job—it’s an art. One needs to master it. Any thoughts or suggestions are welcomed. #sales #insidesales #relationbuilding

Why Do We Need Inside Sales? To better answer to the requirements of the Client every company should hire an Inside Sales Expert. An Inside Sales Expert is someone who finds out who to contact, who is responsible for what with the Client, research background information about the Client and the requirements, supports the salesperson in understanding the Client better, and prepares tailored sales materials for the very first meeting. Without an Inside Sales Expert, relationship with the Client may never deepen to the same level of trust as in cases where an Inside Sales Expert has been involved in supporting the sales process. How have you got help from Inside Sales Expert? #insidesales  #salesexperts #client #research #b2b Pauliina Airaksinen-Aminoff Karina Burgdorff Jensen Pia Hautamäki 🌸Silvio Cardinali Simone Severini Charlotte Bruun Christian Stadlmann Iryna Pushchak Maciej Pietrzykowski

Why Your Next Job Should Be in Sales I’ve spent the past decade building sales software. I lived every day with sales pros and eventually started selling software for my previous company OrderNerd (Acquired by Popmenu) . After all these years, here’s my take: Effective sales demand one thing—alignment. Customer & Solution: This is the baseline. If the customer’s problem and the solution don’t align, every other effort is wasted. Sales Rep & Product: Not every rep fits every product. A rep needs to understand and experience the value they are trying to convey. Sales Rep & Customer: Before having a fact-based problem/solution conversation, you need to connect with the person you’re talking to. Nobody wants to be treated as a transaction, and guess what? It doesn’t have to be that way. Then, when you build your own business, you’ll understand that alignment is the single factor that can either propel or sink it. Lauren Goodell and I are really aligned—we always make sure to tell terrible jokes that nobody laughs at. Sales pros, how did I do? Have I missed anything?

This story is the story of almost every B2B salesperson who survives the first two years in a job. At first they work hard as hunters, making painful, proactive phone calls and drafting cold e-mails. After a while, they have a full book of business to service, after which, somewhere along the line, they transition from hunter to farmer. Ultimately, for sales professionals operating purely in account management mode, the three or four-year mark becomes very dangerous. No matter how well they engage their existing accounts, a certain number of accounts will not renew for any number of reasons. Maybe their main advocate has changed roles or has moved to a new employer. Maybe the competition has built a better mousetrap. Regardless of the reason, the salesperson is inevitably faced with a gap to making his or her quota and a dry pipeline.

What I consider field sales is any time someone gets up off their a** to meet clients or prospects in person. Most inside sales organizations won't do this. Are these organizations leaving money on the table? It can be grueling to dress up, get on a plane, and meet with customers all day. From my experience working with many field sales companies, I've seen that it can be a significant differentiator. It demonstrates the level of support and care that customers will receive when they come on board. And up to a 3x increase in win rates, quicker time to close, and increased retention. This week, I had a conversation with John DiLoreto and the Penguin AI team where we discussed Leadbeam and why some companies should consider field sales. I'll add the link in the comments: