Hey everyone!

Bootstrapped founder here - selling b2b SaaS. still not full-time in our startup yet, but we’ve grown to 30k ARR (8 paying customers, 30 unpaid) since launching in August

I advise a few early-stage bootstrapped b2b startups and wanted to share some reoccurring advice that I’ve given recently that has ended up helping them get their first few sales + further validate & develop their roadmaps.

The below is for those of us without the unfair advantages :) i.e tonnes of capital and connections.

Start Validating

Timeframe : 2 weeks

Target : 50 conversations

KPI: Reach out to 30 people per day for 2 weeks

Work backwards from the problem your business is trying to solve. What KPI’s does it impact at what types of businesses & who is responsible for those KPI’s? Figure out the questions you need to ask to validate the problem, your solution and if people are willing to pay for it. If they are, these conversations naturally end up becoming opportunities.

That will help you figure out who you think your ICP / Persona is - now you know who to go after.

Here is how to get the conversations going:

  • Linkedin - Cold connection request: Hi [insert name], pardon the out of the blue message. I’m one of the founders of [insert your company name]. I’m interviewing [insert their expertise i.e finance] leaders in [insert their industry, i.e tech] to understand how they currently [insert the problem]. We’re using this information to help us further shape our product roadmap, would you be open to sharing your thoughts?
  • Already connected - Hi [name], long time no speak. I recently started [your company name] and I’m trying to validate some ideas. I’d love to pick your brains on what we’re working on if you have a couple of minutes to spare.
  • Communities - find engaged communities where your users are: Hi everyone! I’m in the process of launching a new startup and I’m looking to get some feedback to validate some ideas we have.
    The problem we’re working on [insert problem]. The solution we’re building [insert solution and website if you have one].
    I’m looking to speak to [Insert persona] Leaders - who are responsible for [insert kpi] at [insert target company industry and size. .We’d love to do a quick virtual interview, or if you’d prefer we can send a survey link. Any help or Intros would be greatly appreciated

Depending on what you’re building, you could be able to secure some early wins here. The goal should be to AS FAST AS POSSIBLE, get a customer reference. Figure out what ever it is you can do for your customer and do it for them, even if it’s a service (not SaaS). To get them to be able to like you enough to give a reference of some sort.

Launch & start building pipeline

Timeframe : 8-10 weeks
Target : 40 opportunities
KPI: Reach out to 30 people per day for 2 weeks + minimum 5 touchpoints per target.

When you enter this phase you should have a live product / mvp. Get your landing pages sorted. Spend a week getting them refined and to the point where they add value and build trust. Otherwise, any of the work you do will likely be wasted.

Once you’ve finished this phase then you can start to think about how you change up in your go to market / scale things up.

The trick for outreach is to understand that literally everyone you’re trying to reach, is too busy to speak or has a million other people reaching out to them. here are some ways to get through and get a conversation booked in:

  • Focussed outreach - Purchase LinkedIn Sales Nav & started reaching out (about 25-35 people per day). Try a number of different angles including personalised videos, well-thought-out tailored messages. For the recorded messages, use your phone & record a 45-70 second video introducing yourself and ask the customer how they currently solve the problem you’re working on. Suggest you have some ideas you’d like to share with them.
  • Cold email - Purchase a tool like Apollo ($80 per month). Apollo will help you find who you’re looking for and you can build a 3-4 stage email sequence to put them through. they have some great templates. You can safely send up to 150 emails per day, per team member using Apollo
  • Cold call - Apollo and Lusha can help you find phone numbers for the people you’re trying to reach. Cold calling is hard, but by far the most effective way to get traction in a conversation (like exponentially more effective than anything else other than direct referral). Gong has some good guides on cold calling.
  • Guerrilla marketing - for the right contact (I.E your absolute highest on the list). Go above and beyond. Do things like write a hand written note, or send them a well thought out gift. No one else will be doing this. . . Then follow up a week later with a call or email and ask them if they got it. It makes starting a convo so much easier.

High level Sales Process ( HubSpot is free and should be set up to handle this)

  • Identifying an opportunity
    Initial conversation - haven’t done any discovery yet - ( they’re technically a lead, but they are aware of you at this point )
  • Needs analysis
    Need to qualify their pain points and challenges.
    Try to think of 5-15 questions you could ask a customer. By the time they answer those questions, you should know whether or not they’ll be a perfect fit.
    I like to use the analogy of landing a plane when I think of how I qualify an opportunity. You don’t go from 30k feet straight to landing, you gradually descend when it makes sense to. :
    30k feet: Contextual questions - Help me understand the business and where it’s at, what are the overarching goals (i.e growth, consolidation etc).
    20k feet: Specific questions - What is your team focussed on right now? How is the team structured? Are you trying to cut costs / etc?. If I could give you a magic wand to solve x problems, how would you solve them?
    10k feet: Refined questions - How do you currently solve X. problem? how is your stack structured? What have you done to solve x problem before? How do you think it went?
    5k feet: Closing in questions: If I can do x for you, do you think that would be of value? Would you be open to me putting together a business case for you? Or, would you be open to a pilot / trial of our product?
  • Proposal / Confirm Value
    Building out a 2-3 page proposal + potentially getting the customer onto a structured trial of the product.
    This is the most important step. Both of these actions need to be completely intentional - Proposal needs to contain no fluff. trial needs to meet specific outcomes pre agreed to.
  • Negotiation
    If the customer give you permission to move to this stage, you need to understand their sign off process, reconfirm timelines and start to put together a plan to implement.
    If you understand their budgets and sign off process + if you did a good job in the proposal, this stage should be easy
  • Contract sent
    The deal isn’t done until the contract is signed.
  • Closed won / close lost
    self explanatory.

Key learnings
Block out time to focus on some form of prospecting every day - even if it’s 30 minutes.
Do something the same way 20 times. When you can get feedback, pay close attention to what’s resonating and whats not. Learn from that and adjust. Rinse and repeat until it starts to work better.
Solve a problem - businesses have cut budgets massively. Figure out what your value drivers are (do you save time or money, do you generate revenue, do you reduce risk etc). Get a strong understanding of who you think your ICP is, find out the problems that keep them up at night, and get good at articulating how your solution solves problems / generates value. People don’t have budgets for nice to haves / slow to value - early stage unproven products… We focussed really hard on how fast can we get to demonstrating value, and how fast can we get to positive ROI. If you can’t easily articulate this, you may want to think about how you can simplify your offering.
Persistence - Another cliche, but it really is a numbers game. How many people can you reach out to, can you follow up with them atleast 4-5 times. You don’t need to be annoying, you just need to know that you’re not the only person trying to get the attention of the person you’re reaching out to. Once they agree to a meeting - you may still need 1-3 follow ups per stage of your sales cycle. Don’t give up, it will eventually pay off
Ask as many questions as you can and learn from the objections & the no’s - You’ll get tonnes of them - the worst thing you can do is get disheartened. “you sound similar to x competitor | we’re not focussed on that right now | we already have something that does that”. These are learning opportunities and often they’re superficial. "We have heard of them, this is how we’re different | any reason for that? | how’d that go for you? "

Anyways, I hope that is helpful - feel free to DM or ask questions below!

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