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SaaStr Annual Digest: The Key Takeaways of our Five Favourite Talks

Not being able to attend SaaStr Annual in-person this year was a huge disappointment. Part of the fun is engaging with the Kiwi SaaS community, meeting new people and feeling the energy from the industry. The upside of the ‘At Home’ edition was being able to share the SaaStr vibe with the wider team.


We know many of you didn’t make it to the sessions - too early, too busy, too zoom’ed out, so we’ve got you covered. We’ve summarised the best bits from our five favourite talks below. With a free pass, you should be able to watch the replays.


The 5 Things That Kill Startups After Their Seed Rounds and the Secrets to Avoiding Them


Michael Seibel, Partner & CEO at Y Combinator is a VC legend and always delivers. Last year, he shared insights from ‘A Decade of Learnings from Y Combinator’. This year, his talk on the five things that kill startups was enlightening and actionable with plenty of recommendations. Give it a watch, you won’t be disappointed.


1. ‘Fake’ product-market fit

It’s the most common symptom of startups that fail - product-market fit means that conceptually you’ve built what users want and have healthy metrics.

What to do:

  • pick an honest KPI and stick with it (if revenue, track new users and return users)

  • track retention carefully

  • cap your monthly burn and stick with it

  • consider raising less $ in your seed round to be more careful about what you do

  • start with strong technical co-founders

  • have a 3-month essential role hiring: after 3 months, think about whether you’d be devastated to let this person go

  • force revenue-generating employees to pay for themselves

  • learn about all the bad investments your investors have made

2. Turning your investor into your boss and doing what they tell you to do

What to do:

  • always talk to your customers

  • have real KPIs to get confidence in what you’re doing

  • track retention

  • keep a low burn

  • play in a space where you’ve got strong insights

  • don’t give power to your investors over you

3. Co-founder conflict

This is about how much bulls***t between co-founders hasn’t been cleared away.

What to do:

  • have a tough conversation about how you feel, how expectations are not being met

  • set explicit roles and responsibilities

4. Ordinary vs extraordinary

Copying those around you and expecting success overnight

What to do:

  • embrace that you will get better over time if you try

  • think about habit formation

  • have a set of people you get advice from that are extraordinary

  • set SMART goals and try to beat them

5. Slow product development

What to do:

  • have a product development cycle

  • always collate qualitative and quantitative feedback

  • write specs

  • use product management software

  • have the product brainstorm with everyone when the team is very small

  • give all team access to the customer and customer data

  • understand that motivation is a multiplier effect on talent

  • the person responsible for product is responsible for release on time and scope

5 Ways to Optimize SaaS Pricing and Sales Strategies to Win the Rebound


It is more challenging than ever to secure new customers. Shifting the focus back to your existing consumer base to retain, upsell, and realign pricing could uncover new gains for your SaaS business. This session run by The Boston Consulting Group explores strategic methods for optimizing your biggest return on value.

1. Your customer success team has become more important than ever in this new environment. You want them to be part of the accounts team and setting the targets.


2. Segment your customer base and mine your data for natural consumption patterns - from a sales perspective, you want to master your segmentation and understand what and how to upsell and cross-sell.


3. Be ready for stress on pricing as customers aren’t yet on the other side of the crisis.

  • Design pre-defined offers and pre-approved concessions to be able to cater for them.

  • If you’re proactive, you can solve your customer short-term needs and offer a free 90-day license.

4. Pricing discipline helps protect your position in the market.

  • Set a war room and a dashboard so you can make decisions about accounts, pricing and terms informed with what’s happening in the market right now, looking at your overall metrics.

  • Have clear guard rails around discounts and escalation processes so sales can execute on deals whilst discounts are discussed in a strategic way - is it a valuable customer you’re trying to lock in or are you destroying your price point in the market?

5. Power of free - trials or freemium.

  • Help customers experience your solution at low risk/low cost while they’re working from home. But those aren’t sales, they’re just leads and must be converted to sales.

  • When thinking about your pricing today, think about what will happen when demand returns so you can win the rebound. Give them an easy way to start with you but as they scale back up you want to benefit from their rebound.

7 Must-Haves for the New Customer Journey Playbook


In the same vein, Guy Nirpaz, CEO at Totango, advocates for breaking silos between marketing, sales and customer success to deliver the smoothest customer experience possible and reinvent your customer journey playbook.


3 new realities that are here to stay:

  • Customers are where the revenue is

  • Digital is now at the heart of the new customer journey

  • Focusing on value first and monetisation second

Until recently, customer success was supposed to make sure renewals happen, by showing value way before renewals were due. More and more SaaS companies are now focusing on creating value much faster and customer success is now a mindset to drive value first, so they create success early from the evaluation phase (image 2).


So how do you get there?

If the company is organised around functions it’s very hard to manage a customer-centric approach - a lot of hands off and loss of context. A very functional operating model doesn’t focus on the customer journey, whereas an horizontal operating model enables a customer-first approach.


Customer success is simple: what's the best way to cater for a buyer for our solution?

  • Allow the buyer to decide what’s their path - they’re not all the same so don’t treat them as if they were

  • Whatever you can deliver as value first and take out the heavy lifting for the buyer as soon as possible

  • Same for your users - they don’t use and adopt software in the same way - data allows you to adapt and be relevant to them

Regardless of who’s responsible for what, communications must sound like a single voice from the company.


The Secrets of Market Timing: How to Develop the Right Idea, at the Right Time


This one is a must-watch if you get the chance! Allen Gannett is very knowledgeable and quite entertaining.


Creativity is the ability to create something new AND valuable.

As humans, we both seek out familiarity for safety and novelty for potential reward - at first, people don’t like it, then they like it more and more, then they get bored.


  1. Fringe interest - people who are the deepest in the field like something

  2. Sweet spot - when ideas are familiar enough they’re safe WBA’s with exposure they go from low to high preference very quickly

  3. Point of cliché - overexposure

  4. Follow-on failure - when big organisation take over something that has been trending, but by the time they create it, it falls out of fashion

  5. Out of date

To be successful you need to get the right amount of familiarity and novelty. Consumers don’t want things that have all the bells and whistles and can be enabled by technology. They want the right solution for where they’re at. Best not to overwhelm your users with features.


When it comes to creativity, are you your own worst enemy?


State of the Cloud 2020


The State of the Cloud report is published by Bessemer Venture Partners and covers Cloud macro trends, growth strategies for founders, 2020 predictions, and why they believe the future is forged in the cloud. You can access the full talk transcript and download it here.

  • Technology solutions enabled brick and mortar SMEs to rally and reinvent themselves, reduce social distancing, distance learning, etc. since the start of Covid-19 pandemic.

  • 94% of businesses now use at least 1 cloud solution - we’re truly living in a cloud-first world today.

  • Cloud is eating software - Cloud will become the majority of software within 5 years, totality by 2032. We’re still in the early days of cloud - our industry has a long and powerful future ahead

2020 predictions:

  1. The future of work will be remote - more collaborative platforms will be needed as more and more organisations are going remote, enabling access to talent globally, the knowledge economy will become increasingly decentralised

  2. Privacy debt will be the new technical debt - there is a rift between where privacy should be due to the amount of data companies create and collect and where it is at - consumer data, inner company data, company to company data

  3. The cloud industry will continue to proliferate around the globe

  4. B2B transactions will move online - the B2B market is way bigger than the B2C market, worth $100T annually - reducing friction, providing analytics and data to better drive business

  5. The API universe will drive innovation across all industries

  6. We’re entering the age of “automation at scale”, particularly in enterprise


We hope that you got some valuable insights from this article. For more SaaStr Annual content, last year’s digests contain a wealth of information on everything SaaS: Data Rules Them All, Focus, Focus, Focus, Be The Best Leader You Can Be.

We’ll see you at Southern SaaS 2020 in November.

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