Why Most Sales Onboarding Programs Are Broken (And What to Do Differently)

You put in the effort to hire the right salesperson—so why do so many new hires struggle to succeed?

Most sales onboarding programs are broken. Companies hire experienced reps and expect them to "figure it out," only to see slow ramp-up times, high turnover, and missed revenue targets.

In this episode of Revenue Remix, Summer Poletti dives into why traditional sales onboarding fails—and what to do instead. You’ll learn:

✅ The biggest gaps in most onboarding programs (and how they cost you revenue)
✅ Why the classic “90-day ramp” doesn’t work for B2B sales
✅ How to align sales onboarding with your business goals for faster success
✅ The essential elements of a structured onboarding plan that sets reps up to win

PLUS: Get access to a free list of smart sales interview questions in our subscriber forum—so you can hire smarter AND onboard better.

If you're hiring sales reps, leading a team, or looking to fix your onboarding process, this episode is packed with actionable insights you can use right away.

Related Resources & Links:
This Week’s Blog: How to Hire the Right Salesperson
Free Resource: Guide to Smart Sales Interview Questions (Subscribe for free to download!)
Related Podcast Episode: How to Find a Good B2B Salesperson - Steal 6 Tips From Me

Related Podcast Episode: Grow Your Revenue Without Hiring More Salespeople - Leverage the Power of AI

Related Podcast Episode: Forget AI, These 6 Old School Sales Techniques Will Never Go Out of Style
Book a Free 15-Minute Sales Onboarding Consultation (Let’s assess your process & find quick wins!)

Show notes:

• Connect with Summer on LinkedIn
• Visit Rise of Us for more information about Summer's services or to guest on the show and share your insights
• Episode recorded and edited using Descript
• Repurposed content, such as this description created using CastMagic

Transcript

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Those little metrics. They're going to help your rep. Don't leave them wondering and worrying. This ties back to those metrics. If they have little things they should be achieving, then they're going to know where they stand with you instead of waiting for and dreading that 90 day review. Welcome back to Revenue Remix, a podcast from Rise of Us, where we take a fresh spin on driving revenue growth, hosted by Summer Pelletti, a fractional CRO who works with business owners and leaders who feel held back by outdated systems. This podcast explores how adaptable, unified frameworks can transform static processes, equipping teams to meet evolving customer needs and drive resilient, lasting growth. Each episode features insights from Summer and her guests, offering practical strategies to sidestep common pitfalls and build real revenue momentum. It's time to remix the way we think about growth. Enjoy the show. And welcome back to Revenue Remix, inspiring visionary leaders. I'm your host, Summer Paletti, and if you've been following along, you know that we've been talking about the challenges of hiring the right salesperson. I learned early in my sales leadership career that no one can pull the wool over your eyes quite like an accomplished salesperson, how to attract them, how to assess them, how to ensure they align with your culture and your vision and also somehow how to figure out if they're actually a great salesperson. That's all a challenge. We covered that in my blog this week. So if you need to catch up, go there. There's some good tips in there. I'm also offering on my free online forum, some sales questions that you can ask, like how to ask good questions during an interview that will help you suss out whether you've got a good salesperson or a good actor. So it's not easy to make the right choice for the current and future needs of your business. Thanks. But hiring is only the beginning. You've done all the hard work of finding the right person, but if you don't have a structured, aligned, onboarding plan, you might be setting them up to fail before they even start. Think about it. How many times have you seen a promising new hire struggle because they were handed a company playbook, went through a couple of meetings with HR, with their manager, and then told to hit the phones? Maybe they figure it out, maybe they don't, but by the time they do, you've wasted months and potentially thousands of dollars in lost revenue, and also their base pay waiting for them to ramp up. And the flip side of this, it takes a long time, longer than we want to think, to ramp up and become successful in a new B2B sales role. All those leads in the pipeline? If they were any good, the last guy would have closed them. Without a structured onboarding plan, you might think you've made a bad hire and cut bait before they've even had a chance to become successful. What if you do hire the right person and then you let them go after 90 days because they weren't crushing it yet? And that is the reality for many companies that I see, and it's one of the biggest hidden gaps in sales performance. Companies with a structured onboarding process see 50 percent greater productivity in their new hires. That's 5 0 and 54 percent higher retention rates. Yet so many companies still hire an experienced salesperson and expect that they'll figure it out. They won't, at least not as fast as they could if they had the right guidance. Today, we're breaking down why most sales onboarding fails and what you can do to set up your new hires for success while keeping them aligned with your company's goals and vision. And while we're at it, the rest of the company as well. Ever made a bad sales hire? Ever seen a promising salesperson not live up to expectations? Are you even potentially holding back growth initiatives because sales hiring gives you a bit of anxiety? Then this one's for you. So let's get started first. You have every reason to be worried, and I don't want this to sound daunting, but your anxiety has validity. Most onboarding programs fail because they don't actually prepare salespeople to sell and give them a roadmap for success. Here's what can often happen. The training focuses on the company, not the customer. Sales reps spend the first week or so learning about the company history, internal org charts, HR policies, product features, learning the demo, maybe even learning a call script, But none of that prepares them really for their first prospect call. There's no structured ramp up plan. New hires are often given goals, like start making calls by week two or hit X quota. But there's no clear road map or how to get there. It's all information and no execution. Most sales onboarding is a data dump, PowerPoints, product decks, CRM training, but when the time comes for the rep to actually sell, they're overwhelmed. They're unprepared. They don't really know how to stitch it all together. They aren't given a clear ICP or messaging framework, and that's ideal client profile. Salespeople need to know exactly who they're selling to, what challenges they solve, and how, and how to position the company's value, especially against your top competitors. If they don't know this from day one, they waste time chasing the wrong prospects with the wrong messaging or just coming across. As any other salesperson out there, I would you like to buy my stuff? Nobody wants to get that call. Nobody wants to make that call. They don't get real world selling experience soon enough the flip side of this coin is waiting to get the rep on the phone until they finished learning. And sometimes, especially in financial services or SAS, where you've got Highly intelligent sales reps. There's never enough information. If you give them enough time, they're never going to be ready. I still need to learn more. So we certainly have to nip that in the bud as well. A rep can sit in training for weeks. But until they have live conversations, they aren't really training. If you wait too long to put them in front of people, they lose momentum and confidence. If you think of sales like a sport, you can't really train for a 5K. By reading about it, right? You got to get out there and get some reps in and you're not going to be very fast. Maybe you're going to walk half of it. But there's nothing like real live interaction there's no alignment with customer success or marketing new sales hires should understand the entire customer journey. If they don't know how marketing generates leads or how customer success retains clients, they can't really sell effectively. Ooh, and here's the big one. You know, I always leave this for last. Onboarding stops too soon. Sales training isn't a one time event. Ongoing coaching, deal reviews, and skill development need to continue well beyond the first week or 30 days. So what does all of this lead to? Slow ramp up times, higher turnover, and sales people who are just guessing their way. And in most cases, leadership assumes it's a hiring problem. You have someone who isn't hitting their goals and you think you made a bad hire. But here's the thing, It can also, or instead be an onboarding problem, which brings us to the rest of the conversation. I'm done lecturing you. Let's talk about what you can actually do. Even companies that think they have a solid onboarding process often have, key elements missing that could make it more effective. Summer Pelletti of Rise of Us helps her clients transform by building adaptable, customer focused sales systems that replace outdated models. With these new frameworks, their teams can respond quickly to evolving customer needs, reduce friction, and work as one cohesive unit. This shift equips them with the tools to drive consistent growth. Lowering churn and creating lasting customer relationships. As a result, they achieve sustainable revenue growth that positions them ahead of competitors and prepared for future challenges. Together, you and Summer will create a foundation that not only meets today's demands, but supports long term success. Before we get into what you can do differently, quick story. When I was first promoted to VP of Sales, I inherited a sales onboarding plan that was very detailed and my boss was convinced that it was great. New hires flew to corporate for a week of training. They learned the whole process, the system, the CRM, everything. And then they flew back home to hit the phones. It didn't take long for me to realize that there was something missing. Reps went home all fired up and then fizzled out fairly quickly and became frustrated. I could also see that there were a lot of questions on things that had been already covered in training. They weren't retaining the information I made changes. That made my boss mad, by the way, and eventually came up with what I use today. My clients get a very detailed custom sales success plan that includes initial training, mentoring, shadowing other departments, and milestones. An actionable plan that spans one or two years, depending on that business's length of sales cycle. And today I'm sharing some tips for getting new hires. Set up for long term success and you can steal all of them. I hope you get some inspiration here. Number one, provide mentoring and cross training. New hires need more than just formal training. They need real world guidance from experienced reps. Pairing them with mentors allows them to learn the nuances of your sales process first hand. Hearing those questions from prospects and how to respond to them. Get immediate feedback and support when handling objections. Build confidence faster by shadowing successful sales calls. And also you want to have them see what not to do. You're going to want to see those sales calls that probably could have gone a little bit better. And don't forget your other teams. Alignment starts day one, if that's your culture. And by the way, it should be have the new hire sit with implementation, marketing and other teams, gaining an understanding of what they do and start building relationships internally. Here's how to implement it. Assign each new rep a mentor for their first 90 days or longer. Set up weekly shadowing sessions with top performing salespeople. Encourage peer learning by having reps review each other's calls. You can do that on your sales meetings as well. And here's a side note. As much as I have been recognized as a good coach and a good sales leader, they don't want to listen to me. They want to listen and learn from each other. Peer learning is super powerful. And last set up a schedule to have them shadow with your internal teams during their first month number to create a measurable actionable ramp up plan, telling a new rep to hit quota. By month three isn't enough. A structured onboarding plan should include realistic benchmarks for each stage of the ramp up period. How to implement it. First 90 days, learn the product industry sales process complete mock calls. Day 30 to 60, start prospecting. Book first meetings, refine pitches. Day 60 to 90, close small deals, handle objections, ramp up to full quota, month 3 plus, fine tune approach, expand pipeline, hit performance targets. Now these are samples. You might have a shorter sales cycle and it might make sense to get people calling within their first 30 days. You want to get people on the phone sooner? Have them call their network and their partners and maybe lost clients. Thanks. A little bit lower pressure to where if they say the wrong thing or they kind of flub up a little bit. It's not that big of a deal. Let them know when they should hit their 1st sale, when they should be selling independently from their mentor. What size of pipeline they need to have in order to statistically achieve that quota. Analyze your past sales, even using data from your top performing reps and come up with data backed milestones that are achievable and an AI model can help you do that in a fraction of the time. Anonymize your data loaded in, ask for some averages, use those averages so that your new salesperson is set up for success and they're not, you know, Given pie in the sky goals, this kind of structured process on boards, new hires who know exactly what's expected of them and how they'll be supported along the way, most good salespeople want to be successful. And if you give them a plan, they're going to feel like they've got a shot three align onboarding with your sales cycle. If your average B2B sales cycle is 6 months, but your new hire is expected to hit quota in month 3, you're setting them up to fail. I'm going to tell you a job. I turned down once because it was completely out of alignment with reality. Their current sales cycle was about 6 months and they asked me so what are you going to be able to close in the 1st, 30 days? And I was like, uh, okay, no, so you don't want to do that. Instead, set realistic performance expectations based on how long it actually takes to build a strong pipeline and sell deals that aren't just junk. Your operations folks will like that, by the way. So how to implement it. Adjust ramp up goals to match your typical sales cycle. And that might mean prorating the quota for new reps, especially if they start in the middle of your fiscal year, or if they start during a slow cycle, you know, the seasonality of your business. So you should know when. More sales are going to come in as opposed to fewer track activity based metrics. First meetings book pipeline value before full quota attainment and these are those little bite size goals that they can achieve that is going to give them a little boost of confidence until they're fully selling toward quota. Just psychologically, those little metrics. They're going to help your rep. Provide ongoing coaching so new reps can improve before being judged on revenue alone. Include feedback on a weekly basis when a rep is new to you. Don't leave them wondering and worrying. This ties back to those metrics. If they have little things they should be achieving, then they're going to know where they stand with you instead of waiting for and dreading that 90 day review. There should be no surprises there. Number four, make training and feedback continuous. Onboarding shouldn't be a one and done process. That one week, those three days, that doesn't work anymore. If your sales training ends after the first few weeks, reps are going to struggle when they start facing real world challenges and real world conversations and objections from their prospects. Ongoing coaching is key. Here's how to implement it. Hold weekly deal reviews for the first six months. Or more, depends on your business. Set up regular one on one coaching sessions with sales leaders. Provide access to on demand training and playbooks for continuous learning. And while we're on continuous learning, foster a culture of continuous learning. Even your seasoned reps need to brush up on skills and learn new ones. Especially now, nothing stays the same for very long. And then understand that, especially in the first 90 days, your new hires will be feeling unsure of themselves. Make sure that you're there for them. I recommend higher touch points between leadership and new sales reps than you would with folks who have been in the job for two years or more. Number five, equip reps with the right sales and marketing tools. You knew it was going to come down to this, right? Today's buyer researches online first, and they're not relying solely on sales calls. And research indicates that they're not usually willing to talk to a salesperson until they have distilled down to their short list. They're so far into their buying journey that they're looking for little insights. That is going to help them make their decision based on the 2 to 3 people that they filtered down to using that online research. So, if your reps don't have access to the right tools, content and automation, they're going to struggle to compete. And here's how to implement it. Give new hires a library of sales, enablement, content, case studies, competitor personas. Different blogs, all sorts of downloadable assets, whatever you have that is tailored to each stage of your buying journey. You got to train your rep how to use those things ensure that they're fully trained on your CRM, your automation tools, and digital sales resources align sales and marketing efforts. So reps know how to leverage content in their outreach and also let them know that they can provide feedback to marketing today's buyer expects value upfront, so arm them with valuable assets. Like guides and case studies that can help them provide value and build trust. Number six, teach reps to leverage referrals and partnerships. One of the biggest missed opportunities in sales onboarding is failing to teach reps how to tap into existing relationships. Warm introductions from happy customers, partners, or internal networks can dramatically shorten the sales cycle. And I'm not just talking about their existing network that you're hoping to tap into. I hate to tell you, maybe you already know, um, that never works out as much as you're hoping for. So how to implement it. Train reps on how to ask for referrals from satisfied customers and how to ask consistently. It should become a habit. Introduce them to key partners who can send high quality leads and teach them. Who makes a good partner, so they can go form their own. Integrate a referral and partnership strategy into the onboarding playbook and your sales playbook. Here's the bottom line. Align sales onboarding with your business growth. Sales onboarding shouldn't be just a couple of days of action packed training. It should be a structured, strategic process that sets your team up for long term success. When you provide mentorship, set clear expectations, align your sales cycle, equip reps with the right tools. You're not just improving onboarding. You're improving your revenue growth. It is definitely worth the investment to take a look at your onboarding. Want to make sure that your sales onboarding is aligned with your business goals? I'm offering a free 15 minute consultation where I'll assess your current onboarding process and give you at least one actionable way to strengthen it. All right, let's wrap it up. What's next? If you've done the hard work of hiring the right salespeople, don't let misaligned onboarding slow them down. Here's what you can do today. Audit your onboarding process and look for where your reps are getting stuck and what might be missing there. Create a structured 30, 60, 90 day or more plan. Set clear expectations and give them some milestones that they can hit that aren't just Revenue related. Three, integrate mentorship, real world practice, and ongoing coaching. Training doesn't just stop after week one. Four, align onboarding with your company's growth strategy and make sure reps understand who they're selling to, how they're selling, and what success looks like. Okay, that's a wrap. You can find me on LinkedIn. I am Summer Paletti, rhymes with spaghetti, or all of that stuff I just talked about, you can find it on my website, theriseofus. com. If t com. If this made you think, if you found any insights in here, or reminders, perhaps, I would love a share to your network. I would like a review. It helps me with my reach. And I'm always looking for guests. If you have a great story to share your founder journey, overcoming a business challenge, my network would love to hear about it. Again, you could go to the website and sign up to be a podcast guest and let's do great things together. I appreciate the listen. I will see you next week.