Key Takeaways from SaaStr Annual 2017

I spent the week of February 6th, 2017 in San Francisco attending SaaStr Annual. For those who know me, I avoid San Francisco like the plague (for my own reasons) – but SaaStr content generally delivers valuable lessons – so I figured it would be worth putting up with the city for a few days.

SaaStr was founded by Jason Lemkin 3 years ago, and is an extremely valuable resource for founders and executives. It consists of articles, podcasts, and insights produced for SaaS execs, by SaaS execs, to help each other navigate the trials of growing a SaaS business.

I generally don’t attend these type of “sales” conferences, because they tend to be gimmicky and sans valuable information. This was my first SaaStr Annual, and it did not disappoint. Not only was I able to grow my professional network, I managed to make some strong friendships (even in 3-ish days) and even came away with a lesson or two.

I compiled a list of key takeaways from the most valuable sessions (in my opinion), and thought it would be a good share. I hope you find them as useful as I did:

How to Market to Customers Small, Medium, Large, XL – all at the same time from the same budget.

Presented by Lauren Vaccarello, VP Marketing, Box.

  • Align the sales organization with a clear understanding of the company goals, across all segments you separate by. An example of these common goals are “net new bookings.” Sit together and set targets together.
  • Targets should be set across segments. For example, each segment should set a ARR target for the year, and set what segment (commercial, enterprise, etc.) they want each percentage of their ARR to come out of. You can set these targets in an analytical way by looking at sales cycle burn rate, and pipeline coverage.
    1. Once you walk this through, set targets across marketing and sales. For example, marketing responsible for 60% of smaller customers, while enterprise is responsible for 10%.
  • Assign segment leads in marketing – make it somebody’s job to make sure a segment is successful.
  • Build segment specific messaging. Speak to your customers about what is important to them, and what their pain points are – and allow that to help you build messaging that helps them solve those problems.
  • Offer a trial experience that allows you to do in-app messaging, and tutorial to on board. A/B test on-boarding emails and behaviorally triggered emails. Make the product sticky.
  • Nurture Leads through the funnel. It’s not just email – in app messaging, product usage with marketing automation, and keeping sales looped in on progress is important.
  • Target Enterprise. Figure out who are the companies you should target, sit down with the sales organization on who we should go after, and come up with a targeted list.
    1. Prioritize by pulling predictive analytics – what are the 50 most active account, who is paying attention, who is listening.
    2. Utilize Clearbit IP or Demandbase to figure out what enterprise companies are showing interest.
  • The role of marketing doesn’t end at purchase. RETENTION is important.

Making sure your CAC doesn’t kill you.

Presented by Guillaume Cabane (Segment), Joanne Chen (Foundation Capital), Ashu Garg (Foundation Capital)

  • Dig into your data and focus on tactics that work, instead of searching for some “magic” channel that delivers leads regularly.
  • Think of role model companies like Atlassian
  • Reduce friction of customers onboarding. Make it easy for them to come on board and use your sticky product.
  • Look into micro journeys and analytics on those journeys to figure out where to invest more time/money/energy.
  • Volume/effort should not be confused with results.
  • Use tools to measure CAC. Clearbit for enrichment, MadKudu,, Zapier are all valuable tools to help streamline.
  • Go all-in on content. Have employees publishing on LinkedIN, strategy around distribution on every single post, and have entire team like it on Medium.
  • For Account Based marketing – start small, focus on your customers in a small segment. You can do it with not a lot of money.
  • Try to optimize for pace of implementation. Reverse IP deduction can be done and scored to see if traffic is of high quality.
  • Experiment with CTA with IP discovery/enrichment – high value targets shouldn’t have a signup page, they should have a “request a demo CTA”
  • KEEP MEASURING what’s working, never stop doing so. Don’t get comfortable.

Levers of SaaS Success – Search for Repeatable Scalable and Profitable Growth Model.

Presented by David Skok (Matrix Partners)

  • The simple Funnel model is – Onboard, Retain, Expand.
  • There are two sales motions:
    1. Touchless self-serve (no sales people, based on free trial). This is the freemium model. The key metrics here are Visitors, Trials, and Closed Deals.
    2. Touch – salespeople contact.
  • Concentrate on:
    1. Improve product/market fit.
    2. Find the optimal customer segments
    3. Clear, simple, powerful messaging and positioning
    1. Fix conversion rates before spending heavily on traffic growth. To do this, you can start by
  • Think from a customer’s point of view. Get inside your customer’s head. Think about: what’s the friction and what are your customers concerns from doing what you want them to do.
    1. You are hoping your customers will do something. But the customer is NOT motivated to do it. How do you motivate them? Think about it. Can you trigger, in your marketing, to guide a customer into a buying process?
  • Free tools drive viral spread. This means low customer work required, high value delivered.
    1. Have a trigger for action.
    2. Builds trust through clear demonstration of expertise.
  • MicroFunnels that lead to a WOW moment. For example:
    1. Free trial -> access to current data and import -> invite colleagues -> test feature -> WOW MOMENT
  • Treat your customer like a bank account. Make a deposit first (create value, free content, free tool) -> Create relationship and trust -> end in a consultative/selling situation.
  • Maintain statistics on Productivity Per Rep – quality of sales hires, quality of sales training and onboarding. Invest in sales training, you will get a high payback.
    1. Average productivity per rep
    2. PPR looked at by Rep Tenure
    3. PPR by Individual Rep
    1. Track statistics like:
    2. This can show if you have a repeatable sales process.
  • Assigned Quota vs. Plan & New ARR
    1. Your salespeople should be able to tell you who they are speaking to, how much those customers are worth, and what they should be delivering in terms of ARR.
  • Do REVERSE Funnel Math
    1. 1 closed deal needs 125 raw leads. Then you can figure out how many leads you need to deliver.
  • SPARKETING – Sales, Product, Marketing. Get these meetings going to figure out what the friction points are.

Advice on Enterprise Deals

Enterprise have their own way of buying software.

  • Map through what your process is today.
    1. Map through what you would expect that to change to for Enterprise
    2. Leverage other people’s trials and tribulation.
  • You’re dealing with billion dollar/enterprise customers. It’s not about the product, it’s about connecting with the right people at the right time.
  • Understand early on “How do you guys buy software?”
    1. MSA’s, license agreements are going to be sent over to you to go over. How long does that process take with this company?
  • Lot more preparation on getting that first meeting
    1. Lot of research that goes into who is going to be at this meeting. You will be talking to a lot of people.
    2. Who is in that room and who are you talking to – find out from your ‘business sponsor’ (guy who is bringing you in)
    3. Expect that there are many more people they want to deal with it
    4. Be prepared that you have to go through procurement, IT, security, etc.
  • Once you sign them up, they’re expecting a different level of service (level up).
    1. Make sure your team is equipped to handle a customer like that.
  • Do you have a process where you implement and manage a rollout.
  • Keep milestones of getting the customer onboard
    1. What’s different
    2. How do we execute it.

Lessons Breaking through $5m ARR.

Presented by Laura Bilazarian (Teamable), Louis Jonckheere (Showpad, Fred Stevens-Smith (RainforestQA)

  • Hiring the right type of salespeople, and training them properly is extremely crucial.
    1. The wrong types of reps are expensive.
  • Hitting the wall can happen when you realize you need 3-5 sales reps, instead of the 1-2 you have running your department. The issues are scaling the best reps.
    1. You can get to $5m with 1-2 reps, but it might be harder to scale up from there.
  • Don’t be distracted by logos for hiring your executive team. Don’t go get a Salesforce VP or something.
  • There is nothing more expensive than having sales people that do not have enough leads. Think about if you need more outbound or inbound.
    1. With that, do not just blow up your sales organization and then have to contract. Build the teams around the best people you have.
  • The SDR role is outsourceable.
  • Hire more than one AE at a time to A/B test how they’re working out.
  • You may need different VP’s for different stages of the company.
    1. Someone for 1-25, someone for 25-100. People know how to get from those numbers to the next level.
  • A VP of HR/People is a crucial, superpower hire. This function is massively underappreciated but can be a huge game-changer.
    1. You’ll also need a CFO as you approach this stratosphere of ARR.
  • Do NOT scale the sales organization without the repeatability in place.
    1. Sales humans to revenue added. Quota retainment. Ramp time. And figure that out.
  • Hold your reps accountable. Each rep should get a number, with logos, and ARR attached to see how successful they are. Compare it to previous months and you can figure out predictability.