"If you try to make it about yourself, in most cases it's not going to work — because you're not paying attention to what they really need. This is a two-way avenue. It has to make sense for both of you."
Ivan Sierra, Strategic Advisor: I was looking for opportunities to take my background and experience and bring them into companies that could really benefit from them. There's certainly a need for that type of role within startups, and that's how I ran into Connectd and the work they were doing — particularly with the startup community, trying to bring people with experience and certain backgrounds to assist founders on their journey in a way that was affordable and doable for that type of company, which sometimes isn't in a position early on to bring someone of a certain calibre on a full-time basis. The model that Connectd was using resonated with me, and I started investigating how to get involved. That's how my journey with Connectd started.
Ivan Sierra: I was very strategic from the outset about which companies I was approaching. There had to be a strong match between what I could bring to the table and what the company was doing. So from the get-go, I knew I was going to be able to speak their language. After that, it was really about trying to understand their challenges, their needs, any pain points they were having — and whether there was a genuine match with the founders. I met with all of them. I had several conversations. I produced certain documents for some of them about my vision and ideas around things they were struggling with.
I think giving yourself the opportunity to genuinely assess whether you're a match is critical — because on paper something can look right, but honestly, this is a two-way street. It has to make sense for both parties. And if you make it all about yourself, in most cases it's not going to work, because you're not paying attention to what they really need.
My approach was simple: an introductory message saying I've seen your company, I've seen your deck, I have significant experience in these areas, and I'd like to have a conversation to see if there's a fit. If there wasn't a fit, we still had a good conversation. I didn't try to sell myself with long presentations or position myself as someone who had all the answers. The first aim was always an honest conversation — where are they in their journey, what areas need the most help, can I contribute there, what are the major pain points, and then start exchanging ideas about solutions. Frank, honest conversations. That's what worked.
Ivan Sierra: The roles where I'm having the most impact are helping companies enter new markets. I'm working with two companies in the UK that are looking to bring their products to the Americas — North America and Latin America. I have a lot of experience in these markets. I've worked in them my entire career. Having that knowledge helps them bridge a lot of potential hazards when you're trying to enter a territory you don't know.
My familiarity with their technology and product line from my prior roles means I can not only support them in entering a new territory, but also help them identify the right ideal customer profile, reach the right personas, and land their initial lighthouse customers.
Ivan Sierra: It was about understanding their value proposition, understanding the product very well, and making sure we agreed on who the ideal customer was and which personas we needed to be engaging with.
In terms of cadence, I have weekly or biweekly calls with most of them, and we exchange a lot of emails. Nothing is set in stone — it's more needs-based. Some weeks we've had several calls, exchanged many documents, and things move fast. The next two weeks there might not be much happening. So you have to be flexible with the rhythm. But constant engagement is what makes them value you. You're there, you're interested. If I don't hear from them, I'll check in — is there anything coming up I can support you with?
It's a partnership ultimately. You're an advisor, but it's not only on them to tell you what's needed. It's also on you to further the conversation and pick their brain about what else can be done. We have a WhatsApp group, so it's not all formal — sometimes it's "Hey Ivan, I just saw this, what do you think?" at ten o'clock at night. It's a mix. Every company is different, every founder is different, so you have to be flexible in how you communicate, how you stay engaged, and how you progress toward a common goal — which is ultimately what it's all about.
Ivan Sierra: The first thing I did was review all the startups. I only focused on those in verticals or business areas where I had relevant background and experience — that brought the list down considerably. Then I started filtering further: are they at a revenue stage? Are they at MVP stage? Which ones did I feel most comfortable with? I used the platform tools to narrow it down and build what I'd call my target portfolio — maybe the top 50 that made the most sense based on where they were in their journey, what business they were in, and how much information they'd provided on the platform.
From there, I used the chat feature to reach out via DM. The message was simple: I've researched your company, I'm in an advisor role, and based on X and Y, I think we should have a call and see if there's a fit. That's how every conversation started — through the platform, using the DM function, exchanging messages, setting meetings. After that it moved to Zoom or Google Meet, but everything started from the platform.
I've talked to many more companies than the three I've secured roles with. In some cases there was no interest because they were at a different stage. In others, there simply wasn't a fit. And in some cases, I had to decide who to prioritise — where could I make the most impact? Because you have to be honest with yourself. You cannot take on 20 companies. You'd be doing a disservice to them and to yourself.
Ivan Sierra: To founders: talk to people. You have 15 minutes. I understand founders are busy and stretched — but talk to people. You might be surprised what you find.
To those interested in an advisory or board role: two words are key — proactive and flexible. This is on you. For the most part, you are going to be looking for opportunities; they are not going to come looking for you. And be flexible in terms of how you work with these companies, including on compensation. Maybe what you had in mind isn't what they can offer right now — but maybe they can get there in the future, or maybe you find a better arrangement than you originally imagined. Be proactive and be flexible.
Ivan Sierra, Director of Strategic Accounts, Industrility | Strategic Advisor, CX Assist Ltd
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