Without sales, your startup dies.<\/p>\n\n\n\n
Yet, sales is all too often a dirty word. One reason for this is because early sales managers repeatedly make avoidable mistakes on the journey to go-to-market fit.\u00a0They overpromise and underdeliver.<\/p>\n\n\n\n
They go for the sale without caring about what the customer needs in the first place.<\/p>\n\n\n\n
They get salesy<\/em>.<\/p>\n\n\n\n It doesn\u2019t have to be that way. Below, I share common pitfalls and techniques in four fundamental areas of startup sales. We\u2019ll hit:<\/p>\n\n\n\n In each section, I\u2019ll also aim to give advice about how to repurpose first version of these assets as you evolve your go-to-market strategy because with limited resources, you should make key assets, like sales playbooks, fungible.<\/p>\n\n\n\n I wrote this because sales isn’t a magic switch you turn. SaaS founders and operators need help structuring and understanding the importance of sales basics. <\/p>\n\n\n\n But it is also a lot of text. So feel free to look around and jump to the sections that are most relevant to your team. Here\u2019s a summary on the content to make it easy to jump to the part you\u2019re most interested in:<\/p>\n\n\n\n Or jump right into it!<\/p>\n\n\n\n Your startup sales playbook is your evergreen guide to securing happy, paying customers. It’s a collection of your processes and practices that help you achieve your sales targets and continually improve your sales organization.<\/p>\n\n\n\n But where do you start when you want to create your first one?<\/p>\n\n\n\n Your earliest customers will shape your thinking, your next few moves, and even your cash flow<\/a>. Without knowing it, you\u2019ve started to lay the groundwork for your sales playbook and your go-to-market engine.<\/p>\n\n\n\n Here\u2019s what I mean\u2026<\/p>\n\n\n\n Remember the first customer you closed? How after that payment was processed or that service order was signed, you set your sights on cloning that customer. <\/p>\n\n\n\n \u201cGo get X-number more of Y-type customer,\u201d right? <\/p>\n\n\n\n Nod your head if you\u2019re guilty of saying or thinking this \u2014 for many startup sales organizations this is where strategy starts and ends.<\/p>\n\n\n\n For many sales organizations \u201cGo get more X-type customers\u201d is where sales strategy starts and ends.<\/p>\n Tweet this quote<\/a>\n <\/blockquote><\/p>\n\n\n\n Because you\u2019re trying to figure out how to replicate and quicken your successes, it can be tempting to build your sales playbook around your first customer or an early customer that contributes significant revenue and product feedback. Or a customer that simply makes you feel good.<\/p><\/p>\n\n\n\n Beware of this bias though. Spend time striking the delicate balance of understanding who you are and who you want to be. Next, start to write this down \u2014 along with the processes and practices you need to execute consistently to achieve your vision. And voil\u00e0, you\u2019re on your way to an early sales playbook that can focus and strengthen your commercial operations.<\/p>\n\n\n\n Here are a few prompts to help you get started on the why<\/em> (which you’ll want to do before interviewing sales candidates — the good ones will ask these kinds of questions):<\/p>\n\n\n\n And now, some on the how <\/em>and the who<\/em>:<\/p>\n\n\n\n A thorough introspection, even if incomplete, makes it easy for future hires to succeed. Don\u2019t expect a new hire in sales (or any domain, really) to come in and solve your puzzles and problems. I see people make this mistake for VP, C-level, roles, so why would you set this precedent and make this mistake for individual contributors or even junior salespeople?<\/p>\n\n\n\n This exercise also gives you the opportunity to ensure that from the get-go, your commercial team is operating in a way that is aligned with how you want to run the business \u2014 instead of allowing new hires to apply old or inappropriate sales methodologies that will burn leads and shape customer opinions.<\/p>\n\n\n\n A perfectly crisp sales playbook may feel unattainable because like most startup operations, you\u2019re learning about your ICP and your messaging as you sell. <\/em>In fact, when I asked Khris Fenton<\/a>, Director of Sales Enablement and Operations at WealthEngine for his definition of a sales playbook, he laughed and said, \u201cThat thing I want to do but simultaneously don\u2019t think I\u2019ll ever complete.\u201d\u00a0<\/p>\n\n\n\n Of course, no one wants a shoddy or incomplete sales playbook. Your go-to-market strategy and how you articulate it to your sales team needs serious and regular fine-tuning (and at some point, a full-time or even team of certified, top-notch mechanics).<\/p>\n\n\n\n If you\u2019ve spent time massaging a first version of what I\u2019ve described above, my next advice is three-fold:<\/p>\n\n\n\n As your understanding of your buyers matures, you should get as specific as you can without building in details that will quickly be forgotten or dated. Keep in mind that the best and most motivated salespeople will be curious for industry and product information in order to sell better, faster. More concrete information on the industry, guidance on messaging, and customer success stories will help future hires ramp faster.<\/p>\n\n\n\n Your playbook can evolve to include specific detail on:<\/p>\n\n\n\n To me, a healthy startup sales playbook has consistent material that is consumed daily and iterated on monthly. I find that a lot of the battlecards, buyer personas, and templates are superfluous exercises to show commercial progress. While you should of course put the energy into giving smart guidance, beware of growth techniques or candidates that sell a magic pill.<\/p>\n\n\n\n The other key indicator of a useful sales playbook is its narrative. As your content and sales tools begin to grow, it can be challenging to weave together the core components in a way that is consistent. That\u2019s why I suggest spending significant time on the why <\/em>of your sales organization. If your sales team has a way to evaluate their own behavior and customer interactions against the organization\u2019s expectations and standard operating procedures, they\u2019ll be better situated to course correct with available resources.<\/p>\n\n\n\n Finally, you\u2019ll begin to bake in some sales templates and tools. I\u2019ll talk more about sales ops later on, but my guidance is to work on building your first sales tools quickly and one at a time. It will likely happen organically \u2014 a new hire will ask questions like \u2018how can I overcome an objection about a missing or inadequate feature\u2019? So, you (or likely your first sales manager) will begin to create assets like this:<\/p>\n\n\n\n Which can get even further fleshed out into guidance\/assets like this:<\/p>\n\n\n\n Now that you have a sales playbook with concrete answers to questions sales candidates will inevitably ask, you\u2019re ready to begin hiring. <\/p>\n\n\n\n Whether you have help from an HR department or you\u2019re a lone recruiter\/sales manager\/quota-carrying badass, I encourage you to follow a structured process. This will help you combat the feeling of being \u2018sold\u2019 during the interview process and ensure you’re evaluating characteristics of high performers.<\/p>\n\n\n\n This is the process I use to hire a full-time Account Executive at ChartMogul:<\/p>\n\n\n\n Some organizations use scorecards and ATS systems like Recruitee<\/a> to track interviewer feedback and candidate progress, but don\u2019t apply unnecessary structure.<\/p>\n\n\n\n Ready to schedule those interviews? Not so fast. <\/p>\n\n\n\n Before you talk to the first candidate, earmark the key characteristics you expect candidates to showcase during the application process. In addition to evaluating startup sales experience and product knowledge, candidates should exhibit specific characteristics that will help them win over your buyers and excel long term. This will make sure you hire a great fit candidate \u2014 and help you avoid the \u201cshiny object\u201d syndrome where you get excited about a candidate because of a great logo on her resume.<\/p>\n\n\n\n The average sales organization salesperson turnover rate is now 34%, with \u201cinvoluntary turnover up nearly two-thirds of that number.\u201d The same research suggests that one in ten companies experience turnover rates above 55%. The new average time for reps to ramp to productivity has reached 5.3 months. On average, only 67% of reps are making quota, down from 74% in 2012. No matter how you spin it, the data reflects an unfortunate trend.<\/p>Anthony Chaine<\/a><\/cite><\/blockquote>\n\n\n\n And for next-level startup sales hiring, list out those characteristics. Some of those characteristics depend on your sales model and your industry. You can pinpoint those characteristics by reflecting on sales methodology (more on that later).<\/p>\n\n\n\n Here\u2019s what I mean:<\/p>\n\n\n\n This is a sample list of characteristics we evaluate during our AE hiring process:<\/p>\n\n\n\n By itself, it\u2019s a fine checklist. But have you ever had that nagging feeling after conducting an interview? Maybe something bothered you but you just can\u2019t put your finger on it? By defining those competencies and providing evaluation guidelines, you can make sure that you, or your HR team, aren\u2019t checking those boxes simply to get a body in the door.<\/p>\n\n\n\n It takes ~50 days<\/a> on average to hire a sales professional. Don\u2019t rush it. Salespeople are skilled practitioners of selling themselves too.<\/p>\n\n\n\n One of the essential pieces you have to get before you’re ready to hire is to define the “why” of your sales organization:<\/p>\n\n\n\n The best salespeople want to believe in what they are selling. And even more so, they want to believe in the business they are building by selling your product\/service.<\/p> So if you need to bring on the right salespeople NOW, show them how you\u2019re making a difference why they should drop everything to get on board and be part of your mission.<\/p>Amy Volas<\/a><\/cite><\/blockquote>\n\n\n\n Here is an example of how we evaluate one competency in the interview process. You can ask these questions in a video interview or even to a candidate\u2019s supplied reference:<\/p>\n\n\n\n It\u2019s possible, that you find a candidate that you\u2019re ready to hire, but who does not excel at every targeted competency. With a structured interviewing process like this, you can identify areas of potential concern and proactively work them into your onboarding and management strategy. If there is doubt, though, stop and close out the process.<\/p>\n\n\n\n There is a lot of competing advice about whether you should hire a sales candidate with nearly identical skills and experience and\/or an existing network of contacts. For example, if you sell healthcare wearables to hospices and palliative care organizations in the U.S., should you only hire from that talent pool?<\/p>\n\n\n\n In truth, I\u2019ve seen this formula take off and also fail spectacularly. If you have a particularly niche product or require relationships with larger channel partners (like Salesforce, Oracle, Microsoft, Atlassian, etc.) it might make sense to hire from the same pool, but it\u2019s also harder and more expensive.<\/p>\n\n\n\n For most SaaS companies, I would recommend hiring salespeople who have worked similar deal sizes and sales cycle lengths. It improves ramp time and helps them stay engaged.<\/p>\n\n\n\n The best practice for SaaS companies is to hire salespeople who have worked similar deal sizes and sales cycle lengths. It improves ramp time and helps them stay engaged.<\/p>\n Tweet this quote<\/a>\n <\/blockquote>\n\n\n\n For example, if I hire someone that was closing deals on a 15-30 day sales cycle and my sales cycles are 6-9 months, I run the risk of that person a) not being successful and b) getting bored\/being a retention risk.<\/p>\n\n\n\n It can be a very expensive and painful mistake to make. Hopefully, by now I\u2019ve debunked the idea that anyone can sell at your startup. Like any critical role, executing a planned hiring process will help you hire and retain top talent.<\/p>\n\n\n\n For further resources about how to structure sales compensation plans, I recommend: SAAS Sales Compensation Simplified<\/a><\/p>\n\n\n\n Stick around a group of battle-tested sellers long enough and someone is sure to tell you how their blue sheet helped them nail that RFP process last quarter.<\/p>\n\n\n\n Miller Heiman<\/a>, Sander<\/a>, SPIN<\/a>, Challenger<\/a>, MEDDIC<\/a>, SNAP<\/a>. There\u2019s no shortage of options if you\u2019re on the hunt for a sales methodology.\u00a0<\/p>\n\n\n\n Unlike a sales process, which focuses on defining the steps or stages on the path to purchase, a sales methodology offers a framework for how sales reps can approach each of those stages to win the deal<\/p>Jacco van der Kooij<\/a><\/cite><\/blockquote>\n\n\n\n Your sales methodology defines your approach to the buyer-seller relationship and how your team solves prospect problems. A defined sales methodology is the foundation of your sales organization \u2014 and should come before your sales model or process. <\/p>\n\n\n\n For startups, applying this much structure may seem counterintuitive or even like a waste of critical resources. Perhaps this is because, as Kooij goes on: <\/p>\n\n\n\n Most of the most popular sales methodologies are trademarked and were created by sales consultants and trainers, who wanted to define their own signature approach. Unfortunately, this means many of the methodologies you\u2019ve heard of are really products being sold to you.<\/p><\/blockquote>\n\n\n\n Here\u2019s why it\u2019s so important though.<\/p>\n\n\n\n Your startup sales methodology grounds your decision-making process. In sales (and startups for that matter), every day, every call is filled with countless decisions. How should I frame this? What should I highlight in my demo? How will the customer respond? What are the customers priorities and how can I communicate effectively? When is the right time to follow up and what should I say?<\/p>\n\n\n\n Process can help you answer some of these questions but methodology gets to the heart of the matter. A well-defined sales methodology brings cohesion to the sales process and arms your sales team with a compass for what to do when a new decision or question arises to which there is not an obvious answer. If done well, it can help eliminate that paralyzing feeling of what should I do next <\/em>or what if I do or say the wrong thing.<\/em><\/p>\n\n\n\n It depends.<\/em><\/p>\n\n\n\n To start, have a serious think about what the selling and buying experience was like for your first few customers. You want to employ a refined methodology that is most aligned with your prospective customers.<\/p>\n\n\n\n From there, do some research. And be sure to put that research into context. Know that the Challenger Sales model<\/a>, for example, is about building consensus with various stakeholders in a large enterprise sale, so if you are hunting mice<\/a>, your methodology shouldn\u2019t involve educating the customer about their problem.<\/p>\n\n\n\n Don\u2019t feel like you have to latch onto every piece of advice within a methodology, but as your decision will be the foundation for your sales organization, it\u2019s important not to waver or to introduce frequent changes.<\/p>\n\n\n\n Too many startups expect salespeople to be immediate and consistent star performers. One constant, regardless of what industry your startup is in, though, is change. As your sales playbook, markets, and products evolve, you should expect to invest regularly in the development of your sales reps.<\/p>Andy Farquharson<\/a><\/cite><\/blockquote>\n\n\n\n Document and exercise your methodology. One way to make sure your sales methodology runs deep is to conduct regular role-playing and coaching exercises. Our team chooses a tough customer call each week and workshops key inflection points. It\u2019s a standing commitment but well worth the investment \u2014 because we know practice makes sales practitioners better.<\/p>\n\n\n\n By now I\u2019ve asked you to document an entire playbook, your sales hiring practices, and a sales framework and we haven\u2019t even introduced process or technology. Who manages all of this?<\/p>\n\n\n\n There\u2019s a reason startup sales and revenue ops are so prevalent in most B2B sales organizations \u2014 it\u2019s a lot of moving parts. <\/p>\n\n\n\nTable of Contents<\/h3>\n\n\n\n
\n
\n
\n
Your first sales playbook<\/h2>\n\n\n\n
![\"Early](\"https:\/\/chartmogul.com\/blog\/wp-content\/uploads\/2021\/06\/lh--t__CR5KDb__l-ClJQRzKKQrPTjQxQeELpzKdxp_IifG2vm1GTNp3j4mlWNRLA13QGdzMcQ0rgRUJOgXynUF2NyBvqeCrBDzKj6DfakTVroRkx4TS2eAf34kg60vz_7zlzx4fLsakwMC.png\")
\n
Your second sales playbook<\/h3>\n\n\n\n
![\"A](\"https:\/\/chartmogul.com\/blog\/wp-content\/uploads\/2021\/06\/lh--t___2T5ukZZ0LrVaS5-jbXN4rHQrJZReo7ewZIdD0rIypm02pLcgmS6pX6ErB-KCUQN6cXs6qu2lEtv_qIDN4Mij90p33Vwvi76ImsVOwhsrzBE6Ib8BVia4oz9hfbMc8DmgFaQdPHS.png\")
![\"Example](\"https:\/\/chartmogul.com\/blog\/wp-content\/uploads\/2019\/09\/in-house-objection-handling-1024x552.png\")
<\/a>
(Click to zoom image<\/em>)<\/figcaption><\/figure><\/div>\n\n\n\nSales hiring pitfalls and must-dos<\/h2>\n\n\n\n
Characteristics of high performers<\/h3>\n\n\n\n
![\"Example](\"https:\/\/chartmogul.com\/blog\/wp-content\/uploads\/2019\/09\/Sample-interview-questions-startup-sales.png\")
<\/a>
(Click to zoom image<\/em>)<\/figcaption><\/figure>\n\n\n\n\n
Startup sales methodology and why you can\u2019t wing it<\/h2>\n\n\n\n
Which sales methodology is right for me?<\/h3>\n\n\n\n
![\"Five](\"https:\/\/chartmogul.com\/blog\/wp-content\/uploads\/2021\/06\/lh--t__SLJkcv1EEj0ygvRFDKftZ2HtFDs-wMNkCkOd3omIQcgr-ux9ick3dJJfAi22cJwJiP0hLMKVX6a3et4SHF3z5NUXZLTZ2wXNtevTgZajO7ltC4TtM9AlXEgvJ5htdL8hdlLQ9yNF.png\")
Source: Christoph Janz<\/a><\/em><\/figcaption><\/figure>\n\n\n\nCoach regularly<\/h3>\n\n\n\n
The sales ops balance<\/h2>\n\n\n\n
![\"Change](\"https:\/\/chartmogul.com\/blog\/wp-content\/uploads\/2021\/06\/lh--t__d30ZgWutuysrZxAu92njkjfcR1easyH1XQXq4QS_dU7eaIqTZaHxS3yKk29mDu69cGhIipCU89wRikxChfF8YeOv8MV1oM2gnT6QFt0q8QBoV4gUjYUjaC9J4s1U63XGKcYdux-1.png\")