This article is by Peter Kazanjy, co-founder of Atrium and TalentBin (acquired by Monster Worldwide in 2014). It's excerpted from the sales onboarding and training chapter in his book, Founding Sales, which tackles everything founders and first-time sales staff need to know about acquiring early customers, building and scaling winning sales teams.
“The lack of rigor around sales onboarding at so many organizations astounds me,” says Peter Kazanjy, co-founder of recruiting software firm TalentBin. Especially considering how much time companies pour into finding the right people.
Once you've pulled the trigger and hired salespeople you like, your entire focus needs to be on getting them up to speed as fast as you can. And the stakes couldn't be higher.
Early on, your biggest cost is the opportunity cost from missed or even just slow sales. In an environment where the salespeople you haven't hired yet are probably losing you $50,000 to $200,000 a month in foregone revenue, time is of the essence and there's no room for error.
What struck Kazanjy as he was building TalentBin's initial sales team was that missed or dissatisfied customers would rob the company of tremendous future value because happy users recur, proliferate, and refer others. The benefits yielded by every sales win are vast and unknown. Consider then the cost of 30 to 50% of your sales reps flaming out (which, believe it or not, is average). He also realized that the best weapon against sunk costs was an ironclad onboarding program that would immerse new sales hires in the right mentality, and all the resources they'd have to draw on to land and close business.
In his book, Founding Sales, Kazanjy looks back at the onboarding tactics that ended up making the biggest difference during his time at TalentBin. Here, he shares the actions he recommends all B2B startups take to build not only the most talented sales team, but the best-prepared sales battery possible.
Organizing Your Own Sales Boot Camp
I have a firm conviction when it comes to onboarding: It doesn't matter how much experience or skill a sales rep brings with them, they need to go through training to work at your company. Cutting corners sets a rotten precedent and will come back to bite you. Every new sales hire should undergo one to two weeks of rigorous onboarding. Depending on how complex your product is, it might deserve even more time.
The most effective onboarding is styled as a boot camp that expedites acclimation to company culture; immerses reps in the product, the business, and the market; gives them a crash course in tools and process; drills them on the skills and lexicon they'll need to use all the time; and aligns them around the same vision for the future.
After you hire right, you must enable right. Position your human capital for success.
Listing what you want to get out of training is one thing, making it happen is much harder. I prefer a university-style onboarding program for new hires with a singular focus on imparting the knowledge required for high-impact sales conversations, and running them through enough repetitions that muscle memory takes hold and their confidence grows.
Ideally, you should be hiring and running reps through boot camp in classes or cohorts. It's a similar amount of work to onboard four salespeople as it is to onboard one. You want to force multiply. Also, classes give them a sense of shared identity and purpose right off the bat — you can emphasize this by giving them names like “Gryffindor” or “The Three Amigos” and having them compete with other teams.
Striking a balance between competition and camaraderie pays off. If one trainee misses something, their teammate will be more likely to help them out and fill in the blanks. And when it comes time for drills, you'll have natural sparring partners at the ready. You want to hire in classes and onboard in classes.
Don't stress on curriculum.
As your company and strategy evolve, your sales approach will need to change. The way you train people can't and shouldn't be set in stone, and you should always be fine-tuning along the way. In fact, when you start out, I recommend dumping everything into a big Google Doc and highlighting sections in green as you cover them.
Sure, this may turn into several docs, and maybe a spreadsheet checklist to track the progress of each class, but even that's still pretty scrappy. Too many companies freeze when it comes to training, intimidated by the labor and thinking that has to go into it. Don't let this happen to you, just start populating the knowledge you think your reps should have and go from there.
The important thing is to have a holistic set of topics to cover and to work your way — exhaustively — through them for every class, adding and removing as you go.
Below are the general buckets that I've included in every single iteration of my onboarding curriculum, that have gone a long way toward building winning sales teams.
Onboarding starts before a hire's first day on the job. When people are headed into a new role, they have energy and enthusiasm around your organization. Channel that into learning. You can assign a significant amount of reading at this juncture. What do they need to know to hit the ground running? Bake it into the homework.
I usually dole out a mix of reading, presentations and recordings of sales calls. At TalentBin, we had a library of recordings of “awesome calls” and “terrible calls” organized by customer type (enterprise vs. mid-market vs. SMB). If you have a customer support portal with video content, share that too. If there are any books your organization is partial to, assign those. I'm a big fan of The Goal to get sales staff into a goal-oriented mindset. Send a list of hyperlinks to these materials, and make it clear you want them to go through each and every one. It's important and non-optional. There will be a test. Don't say something nebulous like, “Review these materials.”
You also don't want to send too much. Make sure all of the pre-work materials you share hit a high bar of quality and relevance. If new reps suspect that they've been given busywork or that they won't actually use the information in their day to day jobs, it will damage your relationship. Shoot for 10 hours of work over a two-week stretch. Make it clear that their progress is being tracked — much the same way it will be on the job. This can be as easy as asking them to highlight sections of a Google Doc as they complete them.
Pre-work serves a couple other purposes. By engaging them early, it staves off new hire cold feet and makes them less likely to take counteroffers from existing employers.
Critically, don't forget to do some pre-work on your side too. While your new hires are absorbing this material, you need to make sure they have the technical setup they need to nail their job from Day 1. Order some quality SWAG.
Every new staffer's desk should look like you were waiting for them to get there with bated breath and you're so glad they're there now.
Culture isn't just one conversation. It's how you demonstrate the way your company executes, what is celebrated and what is censured. Kick it off with a proactive, explicit discussion of what your sales org values and what's not okay. Here are three tenets we presented upfront at TalentBin:
You don't have to be an engineer to operate with an engineering mindset.
We are all the product managers of our sales organization.
Intellectual honesty is paramount.
These three were important because they spoke to our broader culture. The sales team at the company was constructed by engineers who valued using technology to maximize their capabilities. This is a value we wanted the sales team to embody and carry on, encouraging them to identify constraints, propose solutions, test them, rinse and repeat.
We wanted people to behave like product managers so they would constantly be thinking about ways to improve our workflows. We actually called different aspects of our sales process “features” and asked for people to speak their mind on which features should be iterated on, killed or added.
Lastly, the company itself was born out of an initial failed product. We had to pivot our way to product-market fit. But that never could have happened if we hadn't been brutally honest in our self assessments. You have to be willing to declare failure before you can improve, and we wanted continuous improvement.
These are the types of cultural touchstones you want to relay to new sales reps immediately. They should be couched as foundational and unflinching. Having these tenets in place will help you hire, and will make it easy to spot which new employees are really inspired by them.
Frame your culture in terms of company history. 'This is where we started, and this is how we got here. This is where we are, and this is where we're going.'
A robust review of your company's path and your sales team's evolution are important for cultural onboarding and provide a key opportunity to underscore major themes in how you like people to work.
Business and Market Onboarding
Ideally, your company is selling a solution that fits into an existing market but is unique enough to stand out. In order for sales reps to positively present a new, less proven solution, they need to be experts on the market they are selling into, what drives business in this area, and the technical realities of your product or service. This is the only way they will be able to interact with customers as equals — not just vendors.
Early on, you may be able to present this information in a series of slides on people's first day. As you grow though, you may want to design a test to make sure that larger batches of people are retaining this information and record classes and materials for staff to refer to.
Here are the knowledge buckets we tested at TalentBin and the questions we used to achieve comprehensive coverage:
What field does your solution operate in?
How has that field changed over time?
What technology has made a major impact on that field so far?
Who are the major vendors already out there?
Are they tangential to your solution?
For example, if you're in sales automation or the CRM business, you want to know which vendors are offering campaign management solutions that will sit on top of your product. Customers will ask about how your product works with other tools they're using. You have to know them to give a nuanced answer. At TalentBin, new hires got a crash course in the history of talent acquisition, job boards, applicant tracking systems, recruiting agencies, and more.
Business Driver Understanding:
How does your clients' business work?
What are their cost and revenue levers?
What are the metrics used to measure their business drivers?
For instance, if you're selling a recruiting solution, then you need to know what's important to your customers: number of inbound candidates, candidate quality, cost per hire, time to hire, etc. If your product can increase the number of candidates and quality while lowering cost and time, then you're in business. To impart this knowledge, TalentBin held a one-hour class taught by a very talented former recruiter named Brad Snider who had transitioned to sales and intimately understood the business. You can see a video recording of this class here, and the source slides here.
The reality is you can't teach someone the ins and outs of complex technology in a week. So you need to focus on the most important terms that they'll encounter. You want to go over the basic lexicon with them, to understand where they need to sound authoritative to close sales, and to act as a sponge in sales conversations, noting which questions and terms keep coming up so they can learn them immediately.
Generally speaking, these are the three areas you should try to cover early on in your boot camp process. Yes, you want to give people short tests to validate that they're absorbing the material after each section — especially if you're speaking to them remotely or if you're speaking to many people at once. But you don't want to require perfect recall. Essentially, you want them to know enough to have a baseline sales conversation, but assume they will continue to build their knowledge as they speak with more and more people.
If you start teaching people about your solution before they truly understand the problem, they'll have a hard time presenting it in a persuasive, high-impact fashion.
Product and Presentation Onboarding
You want to give your new staff a thorough education in your product, how it works, and how they can describe it in a way that makes it clear, compelling and critical. These are the pillars of holistic product and presentation training:
Initial product walkthrough: Give staff a formal walkthrough of all the minute details of the product. Look at all the key elements of the product and connect them to use cases for customers. Touch on the business drivers each feature impacts. TalentBin used an abridged version of its customer-facing demo, for instance.
Sales presentation: Because you've already assigned recordings of your sales presentation as pre-work, reps should be familiar with your approach. You want to break your standard presentation down into “chapters” to explain why and how you say each thing. Make sure new hires understand the intention behind each chapter. This will make it much easier to drill presentation skills later on.
Customer-facing demo: Train reps on the segments of an actual sales demo. This should be a mock demonstration delivered live to the class in the same style you would use with a customer. This demo should also have sections that correspond to the business pain points your solution fixes. Be clear. Say things like, “The point of this section is to demonstrate features A,B and C, which are designed to help the user with X, Y and Z, solving pain points, M, N and O.” Do this for each section as the class follows along and can interrupt to ask questions.
Objection handling: Reps will hear a ton of objections from prospects, so you can't possibly review them all in advance. Instead, try to fold in common objections or prospect confusions into your presentation and demo training sessions. Sharing an exhaustive list of common objections with reps is helpful, but it's a waste of time to go over all of them during boot camp. Instead, point reps to your canonical FAQ of objections so they can refer to it later.
Competition review: Tackle this after you teach everything else above. That way there will be a framework in place for reps to understand the differences between what you're selling and what the competition is offering.
Tools and Process Onboarding
The modern sales rep should be extremely software and tech savvy. Their average day includes heavy use of email, calendaring, standards like Salesforce.com, presentation tools like ClearSlide, etc. But you can't assume your staff will immediately know how to use any of the tools you provide. And if they don't, they don't stand a chance. Empower them with the following steps:
Provision and configure correctly.
Too many companies overlook equipping new employees with everything they need. It seems obvious, but it shouldn't be taken for granted. It's worth making a spreadsheet or checklist of every single piece of hardware and software that they will need so you can replicate the process for every hire. This includes a desk, a laptop, monitor, laptop stand, keyboard, mouse, standing foot pad, headset, pens, etc.
Getting to this level of specificity might seem odd, but it will help you hit the target every single time, and it's way more important than you think.
As a new hire, discovering you don't have a chair yet can set off an emotional chain reaction.
Having everything at the ready, like it's all been well thought out in advance, sets an expectation of excellence.
For things that can be set up ahead of time, do it. It demonstrates a mindset of preparedness. At TalentBin, this meant that every sales rep opened their laptop to find a Google Apps identity, Salesforce account, Yesware and ClearSlide ready and waiting for them. Similarly, add all new hires to recurring meetings and the proper list servs so they feel like they are immediately in the know.
Configuration can come later, when your hires are already onsite sitting in class. Ask them to set up their work environments together as a group. If you have them set up their email signatures the right way or create new accounts together, they're more likely to do it and understand the logic behind it.
I also strongly recommend creating a spreadsheet checklist for all the configurations you've found helpful. Block off an hour or two with your newly onboarded cohort and walk through the list. At TalentBin, this is the list we used:
Set your bookmarks and set up Google Chrome to your liking.
Create the right email signature and turn on keyboard shortcuts for “undo send,” “send and archive,” auto-advance, and other Inbox Zero Gmail tricks.
Add browser and Gmail plugins for lead generation, Rapportive, Yesware, BCC to CRM, etc.
Set up your voicemail for your phone.
Get Jing or Skitch installed for screeshotting and screencasting.
Set up corporate email on iPhone and Android with the proper security mechanisms.
Set up mobile CRM like Salesforce1 on iPhone or Android
Set up a demo environment in the product they're selling.
This is just an example, and it will be different for everyone. The important thing is not to rely on reps to do all of this themselves on their own. Because they won’t. Or they’ll do it wrong. Just get it out of the way by doing it together.
Train people thoroughly on everyday tools.
You never want to assume that a tool is so easy to use or that so many people are already familiar that they won't need some form of training. You need to cover all of the tools your staff is expected to use to succeed from the most basic to the most complex. You'll see what I mean:
The Browser Especially when you're hiring people fresh out of college, office basics can actually be quite foreign. And if you're hiring more senior staff, there's a good chance they have a lot of bad habits you'll want to iron out.
At TalentBin, we started with the browser — which may seem to basic — but in my experience, it wasn't. We made sure everyone was using Google Chrome because of its speed and plugin support, and trained on the 'Getting Things Done' mindset:
Closing tabs that you're no longer using.
Creating a new window for a new task that may spawn new tabs (to avoid confusion).
Closing windows when a task is complete.
Mastery of keyboard shortcuts.
The idea was to bake in everything that would make reps more efficient, save them time, and cut out distraction.
Email for Sales
Email is extremely powerful, but extremely dangerous when misused. In sales, it's a great way to create multiple touchpoints with clients in a scaled way, to deliver collateral, and to juggle many conversations at once. It can also be a massive time suck, and, without discipline, your reps' inboxes will become a mess of unimportant junk (“Come to DreamForce!!!!”) mixed in with extremely high-value client communications (“Can you send me that contract?”).
The 'Getting Things Done' philosophy is even more important when it comes to email. If there's not a next action on an email, it should be archived immediately. This can be a new concept for a lot of people. Teach it and audit it. If you come up to a rep and see a read, unimportant email in their inbox, ask them about it.
Also, make sure they remove all email push notifications and alerts on their phones so that they aren't treating emails like instant messages. During other work, reps should close their email entirely and work out of their CRM or calendar to focus on the task at hand.
Similarly, you need to show new hires what well-written emails look like:
How to write clear, topical subject lines and ditch common mistakes like,“Hi” and“Quick Question.”
How to use CC appropriately and reply all to ensure thread continuity.
How to compose messages that have sufficient white space and line breaks for readability and how to use bold, bullets and headings to identify key sections of an email so that people stay engaged with the content.
How to call out the individuals you are addressing and any action items for others on the thread.
How to write for searchability using words that stand out so you can easily recall a message from your Gmail archive.
How to proofread — setting expectations around rigor and grammatical excellence in client-facing communication.
Make it clear that all emails sent are being logged in the CRM so they can be audited for quality and format later.
There has to be strong incentive for people to pay attention to the details.
For speed and quality, train people to use templates as much as possible. Common, repeated communications can take up a huge amount of a rep's time. Using templates can be a massive time saver and reduce errors. The best way to reinforce this is to rely on templates yourself as a company or sales leader.
Whenever your company delivers a new feature or product release, provide a corresponding template or tell reps to create their own to keep it top of mind. Also, if an awesome template is created by rep A, make sure it gets stored somewhere central like your wiki or Yesware central template library so it can be used by reps B, C and D too.
Calendaring Like a Pro
In sales, time is precious. Every rep's calendar needs to be a well-honed tool for them to manage their prospects and themselves. Don't assume that people know how to send, decline or accept calendar invitations. Walk through it, and make sure they know how to call out the location of meetings, whether they are onsite or remote. Instruct them to flesh out their invites with agenda items, conference bridge information, and anything else they need to set and meet expectations. The result is much better meetings with fewer cancellations.
Teaching calendar hygiene is the most important thing you can do to ensure your staff manages their time well.
Good hygiene in this case means removing items that are not relevant to free up time slots for meetings, proper prep and follow-up sessions, blocking out stretches of pure follow-up time for pipeline management and inbox maintenance.
I'm a big fan of “calendar painting” where you book and block off the entirety of your day so you can make sure you're spending your time on the correct things. The same tactic will keep your reps focused on the most important tasks at hand and they'll be less likely to get distracted or be interrupted if they know what they should be working on at any given moment. When you haven't allocated your time specifically, you risk having your work dictated by your inbox.
This is where you may end up with more variation in what you need to cover, but there are some important common denominators in this category:
CRM: This is the basis of any high-performance sales organization. It's the central hub of activity, efficiency and reporting. Every time I help a sales team on the rocks, their issues invariably stem from CRM fragility. From the beginning, make it clear that if information isn't in your CRM, it doesn't count. For instance, if you give a demo — it technically hasn't happened unless it's in Salesforce. If an email is sent that didn't get BCC'd to Salesforce, it doesn't matter. Set the expectation now and demonstrate it consistently.
Data Models: The way data is stored in CRMs can be confusing for even experienced reps. Make sure to go through the basic concepts of accounts, how to create various objects and the fields associated with them — like projected revenue and stage of opportunities, size of total opportunity in an account, contact information for the account, etc. Cover how to properly record notes, retire tasks and represent closed, won and lost opportunities.
Key Reports and Task Views: If you have reports or dashboards that are key to reps' execution, make sure they're bookmarked and thoroughly described to new hires. An example is Salesforce's console viewer, which allows people to view and execute tasks. Reports might include pipeline check-ins or the list of demos that have yet to be done in a given week.
Sales-Enabled Email: TalentBin used the Act-On marketing automation suite, as well as Yesware, which was also integrated into every rep's email. This helped the team track email opens and clicks and call up a variety of templates. All reps should know that rigorous record keeping, templating and mass emailing are part of the job. This is the only way you'll be able to track and gain insight into deals. Emphasize why all of this data is useful and necessary — it shows how effective your messaging is, how people engage with your collateral, and whether you need to make changes.
Power Dialing Software: I recommend setting up power dialing software to get people into the top of your sales funnel or to follow up with mid-funnel customers. At TalentBin, we used InsideSales.com's PowerDialer to help reps quickly cycle through prospects, make calls, leave pre-recorded voicemails and send follow-up emails automatically. During boot camp, you want to demonstrate all of this functionality so people are aware of the full capabilities and how much easier the software can make their job.
Enforce your ideal cycle and cadence.
While using tools is important, it's even more so to know when and how to use them during your sales cycle. During training, you need to cover the specifics of your sales organization's process and cadence. Different products require different cycles. Here are the questions you should answer for new reps:
How long does it typically take to close a deal?
Is it a bottom-up or top-down sales approach?
Who is responsible for what part of the sales cycle?
Does a sale usually require multiple presentations, or is it more of a “one call close” process?
Do you need to use trials or pilots?
At what point should a rep know that a deal is not going to happen so that they can save their time?
The strongest sales teams have a solid weekly, monthly and quarterly cadence to their work — things that happen regularly on each of those time frames, like team meetings, pipeline meetings, standups, all-hands and happy hours. No matter what these are, review all of them with your new hires and make the purpose of each explicit.
At TalentBin, our rotating calendar included:
A sales team meeting on Monday to review the previous week's stats and revenue progress, and to share product and customer success, team wins and learnings.
Twice daily five-minute standups to check in on activity, wins and learnings during the day.
A once-weekly pipeline meeting to walk through deals, drive accountability and get feedback.
A once-monthly all hands.
A weekly happy hour at close of business on Friday.
As you can see, so much of this time is dedicated to distributing information and making sure everyone is on the same page. That's what good cadence gets you.
The Power of Drills, Repetition and Shadowing
One of the things many sales orgs drop the ball on is giving reps enough time to practice their key actions. The irony is that sales teams are often full of former athletes.
Just like in sports, practice is more important than actual games when it comes to sales too. The best salespeople are the ones who have committed best practices to memory.
Run sales drills again and again — in teams.
Of all the actions reps take, they need to drill their demos and presentations the most. This is something that should be practiced before they get in front of real customers — there's no need to burn through real opportunities. Just like you broke out and ran through each “chapter” of an effective demo, now you want new reps to do the same.
It works really well to do this in a classroom setting with each person presenting a chapter, then stopping to get feedback from the instructor and the rest of the team. It's a slow process — that's why you only do it once — but it really drills the heck out of the material.
Set up sparring partners.
When you're done with these initial drills, split the class up into groups of two. Have each pair trade off as presenter and prospect. The interesting thing about this is that the "prospect" is truly forced to think and react like a real one would. They have to inhabit the mind of their eventual counterpart in a sale. In my experience, this makes them better consultative sales professionals.
Sparring is useful for getting people to think on their feet as they practice cold calling for lead generation, presentation calls and negotiations. For maximum impact, run your sparring in full “game situation” mode, using whatever tools reps would be using in their day to day. They shouldn't be sitting in a room looking at each other. They should be using a real phone and real presentation software. They have to get used to that.
Encourage pair programming.
I'm not a huge fan of 'riding along' on sales calls to learn. This can be done outside of selling hours with recorded calls during the pre-work period. But there is something to be said for following along as a full cycle is executed. That's why I recommend a type of 'pair programming' where a new hire is paired for a day with a seasoned individual in their same role. They aren't just sitting there listening, they actually participate in the critical work that goes on around calls.
For market development reps, this would mean sitting with someone more experienced as they go shopping for prospects, review and execute their tasks for the day, rip down a call list, fire off follow-up emails, or set up a demo. For account executives, pair programming could mean participating in new opportunity demos, and pipeline management or maintenance.
Bluebirding, ramp and monitoring.
When new reps come into contact with live opportunities, you can't let up on your onboarding focus. It's actually a pretty delicate time, where you have a chance to build up someone's confidence and make them feel comfortable on their own. There are several practices I use to make this happen:
Bluebirds Over Throwaways
When account executives are getting started, assign them 'bluebird' opportunities — that is, prospects that have a high likelihood of closing. These are usually inbound leads with strong qualification characteristics.
As the sales leader, you should still team up with new reps on these calls simply to offer backup in the event they run into something unexpected. Though often the pure availability of support, coupled with strong prep, makes it unnecessary.
Make sure you're not jumping into calls just because a new hire isn't hitting the messaging at an A+ level. You're only there in the event that the wheels come off.
Another helpful tactic is for reps to have a printed script of their sales presentation and demo on their desks as they execute calls — not so they can lean on them like a crutch or recite them verbatim, just a crib sheet to make sure they're hitting the highlights and to prevent being knocked off balance.
The opposite of a bluebird opportunity is a throwaway — a prospect that is unqualified for a deal. Maybe they don't have the sufficient technical setup, or the right in-house user for your product. Chances are they aren't buying. I've seen a lot of companies train newly onboarded sales reps on these types of customers so there's not as much pressure. Makes sense on a limited basis, but it can come back to bite you.
You don't want your reps to get in the habit of treating calls like they don't matter. This can lead to some bad habits. And also you shouldn't underestimate the positive impact of a new rep getting an early win. That's the experience you should try to curate. Throwaway presentations are an expensive form of practice — they consume rep time that could be spent on valid opportunities. It's also not 100% respectful of client time.
Proactive and Ambient Call Review
Don't waste an experienced rep's time sitting in on new hire calls. At TalentBin, we recorded all sales calls using ClearSlide's online presentation system (join.me, WebEx and others have similar functionality). That way, at any point, we could pull a recording and listen to it. To make it easier to surface instructive calls, we had our reps call out and label their particularly awesome or heinous calls and share them with the team. Awesome calls were used for future onboarding pre-work. Heinous calls were played to the whole class so we could discuss what went wrong.
As a sales manager, you should also spend time walking around or sitting close to different members of your sale team. Listen as you work. Your ears will naturally perk up when you hear someone in distress on a call. That way, you're not devoting a bunch of time to babysitting people, but you can swoop in with a helpful suggestion written on a Post-It or a quick regroup conversation after they hang up.
Proactive and ambient review of calls will ensure you catch issues early. Don't worry about dampening reps' morale early on — instead, assure them that the faster they take and use your feedback, the sooner they'll start landing wins of their own.
Taking the Training Wheels Off
As your new hires ramp up, you can dial down the amount of high-touch monitoring and coaching and start relying on a core set of key performance indicators. These are things like hold rates for demos, win/loss ratios for account executives, activity levels at the top of the funnel and more.
While your team's recurring meetings should pick up quickly on negative trends or indicators that your approach needs to be adjusted, it's up to management to take extra time to check in on new reps' KPIs and make sure they're tracking correctly. It's not enough to just go over the numbers, either. You need to get rep feedback on how they're actually feeling in your standard (ideally bi-weekly) one-on-one meetings.
Remember, the biggest cost for a young sales team at a scaling startup is the opportunity cost of missed or delayed sales. Rigorous, thoughtful onboarding will minimize these costs and engender a positive feedback loop, faster time to revenue for new reps, and higher retention.
It sounds like a lot, I know, but given how valuable each and every one of these people can be, it's well worth your money and — above all — time.