What Happens When You Have Braindates with Founders

Feb 14, 2018 | Building Relationships, Hiring, Sales, Sales Coaching, Sales Leadership, Sales Management, Sales Relationships

SaaStr Annual 2018 just wrapped up in San Francisco. After 3 days of non-stop networking, listening to incredible speakers and having many Braindates, I finally have a chance to sit down and reflect on what I learned at this mind-blowing event.  

I had carefully plotted out my 3-day schedule with a mix of sessions about Scaling, Start-Up Funding, and AI,  but, to my surprise, that’s not what I did. What I did do was meet with founders who are struggling with issues around building a B2B sales team. Fortunately, I can watch the sessions I missed online because I wouldn’t trade the last 3 days and all the fascinating conversations I had as the result of Braindates people set up with me 

What’s a Braindate? A Braindate is the creation of a Canadian company called e180. This year, e180 partnered with SaaStr to provide a platform that allowed attendees to request 30-minute mentoring sessions with people who had the expertise they were seeking. As an invited mentor, I put in 3 topics: Building a B2B Sales Team, Mastering the B2B Complex Sale and Strategic Planning to Drive Revenue. Who knew I would be so popular? My dance card for Tuesday was full in no time, and by the end of Tuesday, I was booked for the rest of the event. So, what I learned at SaaStr was more about what founders wanted to know than about what speakers were talking about. 

Below are the 5 questions I was asked the most and my answers, answers to questions they didn’t ask but needed to know, and a few surprises from the event.  

5 of the most asked questions and my answers 

1. How do you hire your first sales rep? 

In a start-up environment, hiring the wrong first sales rep can be very expensive. Here are 3 steps to ensure you’re hiring the right person. 

First, make sure you’re clear about your company culture. Hiring someone who doesn’t fit your culture won’t work. If your values include taking care of customers, don’t hire someone who will sell “ice to Eskimos”. 

Second, be clear about the job you’re hiring for. What skills do they need to have and what resources are you providing? Make sure the candidates understand what they will be expected to deliver and whether they will be finding their own leads or being provided with leads.  

Third, find a company that specializes in recruiting and screening sales and sales management candidates. Don’t take any chances! If you’re unsure of what you need, have an expert help you figure it out. It may seem expensive, but it’s significantly less expensive than wasting time and money on the wrong candidate. We often work with Proactivate when helping a client recruit sales talent.  

2. What type of sales rep should I hire?  

The founders I spoke with wanted to know what kind of sales reps they should hire. They all seemed to have one model or another in their head: relational-transactional-closer-consultative, hunter-farmer, relationship builder-results-driven-dedicated-educator. These are great, but what’s really important is understanding what your current situation is and what you need of the sales rep you are hiring. Forget about the buzzwords and think about your situation.  

If you know nothing about sales, you better find someone who already knows what to do and can do it without a lot of direction. That person can help you build your sales process. That means you are looking for someone with experience and a track record of success in an unstructured sales environment.  

Someone asked me, “What about track-record? What should I be looking for?” Again, that depends on your needs. If you have no sales structure in place and expect the sales rep to find all their own leads, don’t hire a superstar from a mature and structured organization where marketing delivers well-qualified leads all day. You need someone a bit scrappier. A cowboy, who can rope, ride and fix fences without you telling him or her what to do.  

Hire the sales rep that fits the job you have available. Again, ask for help. Find a recruiter who will help define the job, write the job description, find the candidates and screen them with you.  

3. How do I figure out compensation? Pricing? 

I am not a compensation or pricing expert, but that didn’t stop people from asking me how to figure that out. I say find an expert if you aren’t sure. There are a few things that I know need to be taken into consideration.  

On compensation: 

– What is your margin and how much can you afford to pay?  

– How much will someone with the skills you need be willing to work for? 

– With the compensation program you designed, is it reasonable for the reps you hire to achieve the compensation level they need to stick around?  

I recommend checking out Xactly for help with compensation. 

On pricing, the same principles apply: 

– What are your costs (fixed and variable) and how much margin do you need to make? 

– What are your competitors charging for similar solutions? 

– What will your customers pay? 

My friend Mark Stiving wrote a really helpful book on pricing. It’s a great place to start. 

4. What are the best practices in Sales Management?  

Talk about the question that could take a week to answer! The short answer is this; a good sales manager spends 80% of his or her time coaching. That time includes weekly team meetings, regular one-to-ones, and additional coaching and training time as needed. 

– Your weekly sales meetings should include product training and updates, skills training and reinforcement, team progress tracking, and strategy sessions.   

– One-to-ones with each team member should happen as often as appropriate for that individual. This time is for reviewing the funnel and providing support and coaching.  

– If additional coaching is required, set up extra time for ride alongs, problem-solving or listening to calls together. Then if additional training needs are uncovered for the team, bring in a trainer.

I think the most important thing, is for sales leaders to remember that your team gets beaten up all week long by customers and prospects. Don’t waste your time beating up your sales team. If they can’t deliver they need to go. If they can deliver, they need positive interaction that helps them perform better.  

5. What tools should I buy for my sales team?  

I was asked this in the middle of a huge SaaS conference! In my wildest dreams, I couldn’t pick the best ones for your team. But, here’s what I can tell you: 

Your team needs a clearly documented sales process. Whether it’s written in Word or is in a fancy playbook isn’t important. What matters is that you have one. It should lay out the stages of the sale, the activities during each stage, the questions that need to be answered during each stage, and the content that is useful during each stage. 

Your team needs a funnel management tool. It could be an Excel spreadsheet, a SaaS funnel program or a CRM. We often recommend Pipedrive or Nimble for start-up teams. The number of leads you have and the complexity of your sale will determine the appropriate tools.  

The team will also need content to support their sales efforts. They will need articles they can send to prospects, infographics to explain complex ideas or timelines, and a deck of slides with the information they can use throughout the sales process.  

Finally, if you are going to have your team making outbound calls, look at tools that make it easier. Autodialers, for instance, will save time. 

Answers to questions they didn’t ask

You need a Key Account Management Program 

I shouldn’t be surprised, but in several meetings, I had to stop and say, “You don’t need more salespeople, you need a Key Account Program.” These founders were leaving $10s of thousands, in some cases hundreds of thousands on the table because they were focused on new logos and not growing their existing accountsLet’s face it, if you only have one department of Wells Fargo, you have work to do.  

To be fair, several of the founders I spoke with were trying to create account management programs. But, they didn’t know how and had the wrong people in charge. I think this is where that hunter and farmer or relationships builder and closer discussion might come into play. Key Account Management requires a unique skill set. Neither a customer success rep nor an AE who is focused on new logos has what they need to do this job. This job requires people management, project management, information management and relationship building as well as traditional sales skills. The first thing to know is that no one can do this job effectively if management isn’t behind it 100%.

Retaining and growing Key Accounts requires organizing resources across the company to identify opportunities and solve problems within those accounts. This article goes into more details about the process and even has a free download on Account Planning.  

You need to learn to manage your funnel 

Being a sales leader means knowing the path to revenue. If you don’t yet have a funnel in place that lets you see what’s going on at a glance, then it’s time to implement one. Managing your funnel should begin to provide you information about close ratios, sales cycles, and timelines. Without good funnel management skills, it is difficult for a sales leader to manage a team. Which takes me back to creating a good sales process. It is difficult to understand and manage your funnel without a good understanding of the sales process. It may be that you develop the two at the same time.  

A couple of surprises  


There were all kinds of SaaS solutions that did any number of amazing things for any number of industries; too many to tell you about here. But, I do want to tell you about one that got me really excited. I love things that are simple and CloseQuick.ly is just that. Simple.  

When Kevin Quan told me about it, all I could think is “This is going to make my life SO much easier.” Alice and I spend a lot of time documenting sales and onboarding processes with our clients. CloseQuickly is a simple way to make playbooks that are easy to use, easy to modify, and easy to get to (they live in the cloud). Kevin made my day. It took him 5 minutes to get me set up and I’m already creating my first playbook. Woot woot 


Did I mention that I loved the Braindate component of the conference? The idea was revolutionary, the platform was easy and the 6 or so staffers who supported the Braindate area were amazing, fun, and really nice.  

For me, networking at a conference can be overwhelming. Braindate gave me the opportunity to spend positive, focused, one-on-one time with people I really liked and expect to stay in touch with. More importantly, this was an opportunity for founders to ask questions they have been needing to ask. At sessions with hundreds of people in them, there is a lot to learn, but it’s hard to customize. These sessions put the founders in conversations with experts who could answer their questions whether it was about sales, ops, legal, tech, or AI. It was great to watch and participate in. Over 1,000 Braindates happened during SaaStr, which means lots of great learning happening.

Do you want to have a Braindate with the Alice Heiman team and get questions you’ve been needing to ask answered? Schedule a time to chat with us! 

Liz Heiman

Liz Heiman


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