Elephant Hunting: Fintech Sales Strategies for Tier 1 Prospects

Craig’s Note: Every wealthtech firm dreams of landing their first big client to put them on the map.  But most struggle with the sales process due to the sheer size of enterprise clients, their bureaucracy, politics, and long decision-making time.  Our guest author is Linda Wittich, who has 20+ years of experience selling, supporting, and advising firms on enterprise software sales.  This article is the perfect primer for how to improve your company’s sales processes and increase your chances of success at closing your first “elephant”.

Are you a fintech CEO or Sales Executive with top tier financial institutions in your sales pipeline? Are you frustrated that deals are taking forever and often going off-track? If so, keep reading. In this post we will review best practices for landing those elephant accounts in the shortest time possible.

Elephant Hunting             

In sales, we tend to categorize our target firms by size: Tier 1 prospects we call elephants, Tier 2 are deer, and Tier 3 are rabbits. I favor startups chasing rabbits and deer over elephants as an overarching strategy.

However, if the opportunity presents itself, you need to up your game and set the stage for a long-term relationship. If you don’t showcase your leadership, the elephant will eat you for lunch. In a future post, we’ll address how to successfully onboard and nurture elephant accounts.

Reasons to avoid elephants

  1. Tech-Debt: Big accounts require customizations. You will need to augment your solution to integrate with their organization and address their operational policies. Is your platform hardened enough to customize and integrate?
  2. Slow: Big accounts are bureaucratic. You will need to have many meetings to showcase your expertise and the robustness of your solution. Assuming your exec team will spend 10-20% of their time for a solid 6-9 months, is the opportunity cost worth it?
  3. Risk: Big accounts require financial stability. You will need to prove your financial viability for at least five years. Since financial due diligence typically happens towards the end of the evaluation stage, you risk an internal build based on your solution. Will you pass their due diligence?

Reasons to pursue elephants

  1. Revenue: Big accounts have the promise of sizable recurring revenue streams. If you do your due diligence throughout the sales process, you can ensure it’s not just revenue but also profit.
  2. Credibility: Big accounts will result in many smaller wins. You will have instant credibility when selling to smaller accounts, thereby shortening their sales cycle materially.
  3. Funding: Big accounts will enable you to get larger investments. Investors love to see marquee brands adopting your solution.



One of my favorite quotes is from Thomas Edison, “Recognizing opportunity is so difficult for most people because it goes around disguised in overalls, looking like hard work!” Be prepared to put on your overalls, roll up your sleeves and do some hard work. If not, don’t waste your time.

When you sell to a small- or mid-sized institution, you often engage directly with the CEO, and their authority is obvious. This is not the case when dealing with matrixed organizations, and nearly every Tier 1 firm is matrixed. Fintechs who win Tier 1 clients recognize that it is their responsibility to continually educate all buyers on all aspects of the proposed deal, including the firm’s expected business value and their own internal procurement process.


So, what’s the Hard Work?


Do the deck! Every meeting, except the discovery call, requires a personalized presentation. It serves as the artifact for your Business Champion to get others to attend future meetings. Every deck must include the following slides, and the slides must be updated as you learn more.

  • Agenda Slide: Goal, Topics, and Meeting Duration
    • Pro tip: If the client has a different goal and you’re not prepared, apologize and offer to reschedule; don’t wing it!
  • Intro Slide: Names and pictures of all attendees (your side and the prospect’s side)
    • Pro tip: Pictures of themselves and their colleagues put them in a good mood.
  • Our Understanding of Your Objectives Slide: Their business objectives for your solution
    • Pro tip: Stop Talking! Let them clarify and lead the internal debate. Take copious notes.
  • Our Vision Slide: Why you exist (the problem you’re solving) and your future direction
    • Pro tip: You want them to align with your vision and future roadmap; they don’t care about your history.
  • Product Demo: Showcase benefits supported by features
    • Pro tip: Frame your demo in a use case and use the names of specific attendees.
  • Content Slides: Except for the Intro Meeting, you’ll have SME content to review
    • Pro tip: Have your SME present the content.
  • Next Steps Slide: Major milestones and details for upcoming next steps
    • Pro tip: On the first release of this slide, list all potential activities (RFP, info sec questionnaire, procurement, etc.) and let the prospect tell you what to skip.
  • Feedback Slide: Explicitly ask if you met their objectives
    • Pro tip: Explicitly ask, “Did we meet your objectives for this meeting?” then be quiet.
  • Appendices: Engagement Summary and general info on your company and product (history, bios, patents, clients, relevant screenshots)
    • Pro-tip: Let the prospect tell you when they want to review your company history.


Use a Strategic Deal Review (SDR) template! Throughout the sales process, you will be continuously learning. Since winning Tier 1 accounts requires participation of your entire executive team, you need a single reference document to educate them on:

  • RAID (Risk, Assumptions, Issues, and Dependencies) Items
  • Enhancement Requests
  • Buyer names and level of influence
  • Expected value (their business objectives)
  • Phrases that resonate


Update the SDR after every call and review it again immediately before the next call. Novice mistake: you think a rolling notes file is a substitute for the SDR.


You need to prove ROI! Hopefully, you have an ROI calculator to easily plug in standard numbers and provide during the Business Justification Review. If not, develop one! The ROI Calculator is typically an excel file with many pre-built comparisons: your solution versus status quo, your solution versus internal build, and your solution versus most likely competitors. Pro tip: Be transparent and include the cost of their internal resources needed to deploy your solution.

Marry the Execs! This step is often overlooked but is one of the most critical factors for winning/losing a Tier 1 prospect. Neither the salesperson, nor the CEO, can be the only face to the prospect. The salesperson’s main relationship is with the Business Champion, and together they own marrying the execs based on subject matter expertise and personalities. A Tier 1 firm engages with a fintech if they believe in the competency of the entire team. Novice mistake: Your CEO develops a personal relationship with the Business Champion before meeting the P&L Owner.

Tier 1 Prospect Fintech
P&L Owner CEO
Business Champion Salesperson
PMO Lead Head of Client Onboarding
User Community Head of Client Success
Operations Head of Client Success
Technology Head of Technology
Procurement Head of Finance
Compliance Head of Compliance or Head of Legal
Legal Head of Legal


Practice role playing! Nobody likes them, but everybody needs them. Yes, role plays are uncomfortable – you’re being vulnerable in front of your boss and peers, but it’s better than bombing in front of a Tier 1 firm. Role playing ensure your presenter understands the objective of the meeting, is prepared, and showcases professionalism. More than anything else, it boosts the presenters’ confidence level. Pro tip: identify one or more people to play as attendees and ask the hardest questions you can fathom – and stay in character.

Follow-up! This is a three-step process:

  1. The first step is for the salesperson to send a thank you note after every meeting to every participant and include a .pdf version of the slide deck.
  2. Then, after your subject matter expert (SME) presents to their corresponding SME (see Marrying Execs) for the first time, they should also reply to their Tier 1 “spouse” saying it was nice to meet them, share their contact details and encourage them to reach out directly.
  3. The third step is for the salesperson to have a 1:1 with the Business Champion after every meeting to learn about the sidebar conversations and validate you met the objective. Pro tip: CEO and Salesperson should connect on LinkedIn with every person in attendance. Big deals often go dormant, and you want people to remember you.


Follow Your Sales Process

Now that you’re committed to not being lazy and doing the hard work, let’s do a quick review of the sales stages. All sales, regardless of size or complexity, follow the same process:

  1. Discovery
  2. Interest
  3. Evaluation
  4. Negotiation
  5. Closing


The Tier 1 difference is the number of buying influencers and the level of detail in their due diligence process.


This is your first leadership exercise. Your salesperson must insist on a 15-minute discovery call and not immediately go into a demo. You must reinforce that this prospect is important to you, and by learning their business objectives, you can ensure it’s a good use of their time – and stick to the 15-minutes!

The primary purpose of the call is for the salesperson to build rapport with the Buying Champion. You also want to validate that your solution matches their expectations. You are setting the cadence that before every meeting, you are entitled to know the attendees, their roles, and their levels of influence. Pro tip: If the prospect has unrealistic expectations or it’s a total product mismatch, be direct. Often, the Buying Champion will still be interested in your product, but you must effectively reset their expectations.

Intro Meeting

The purpose of the Intro meeting is to learn about the client, get agreement on their expected value, and to engage them enough to move to the Evaluation Stage. It is not to close the deal!

The best way to get your client to like you and your product is to get them talking early on. Typically, this occurs on the ‘Our Understanding of Your Objectives’ slide. Your demo script should point out the benefits supported by the features, not the other way around. Novice mistake: Attempting to secure a date and time for the next meeting. Your call to action is simply an approximate date for the salesperson to follow up with the Business Champion.

Evaluation Stage

This is the most critical part of the sales/buying process when dealing with Tier 1 firms. You need to prove your competency in each area and your listening skills. After each meeting, update the RAID list with your internal SMEs and share with the Business Champion at your prospect.

Expect to have three sessions for each group: 1) Showcase your expertise, 2) Learn their specific requirements, 3) Agree upon in/out of scope items.

Divide the participants at evaluation meeting into two categories; those who can vote ‘yes’ and those who can eliminate you by voting ‘no.’ Pro tip: Work with the Business Champion before each meeting to identify who has what votes, their level of influence, and their preferred communication style.

  • User Group (Yes vote)
  • Operations Group (Yes vote)
  • Revenue Group (Yes vote)
  • Service Group (Yes vote)
  • Business Justification Group (Yes vote with the greatest influence)
  • Tech/Arch Group (No vote)
  • Compliance/Reg/Privacy (No vote)
  • Company Review (No vote)


Novice mistake: you skip the standard deck when dealing with the ‘no’ vote groups.

Pro Tip: Keep slack open but only slack the presenter with critical in-the-moment feedback. 


Negotiation and Closing

You’re almost there and it is not the time to relinquish your leadership role! As you enter the Procurement and Legal process, require kickoff meetings. Once again, use the standard deck that includes their pics, business objectives, and recap previously held meetings. Insist that the P&L Owner attends kickoff calls and that the Business Champion attends all calls.

The purpose of the Procurement Kickoff Call is to make it absolutely clear that you intend to negotiate all business terms before negotiating financial terms.

The purpose of the Legal Kickoff Call is to agree to use an Open Items list and Term Sheet before redlining.

Pro tip: If the evaluation meetings did not go deep enough for you to lock in the implementation fees, do a paid Requirements SOW concurrent to completing the service agreement.


Key Take-Aways

There you have it, a detailed review of what to do when prospecting top tier financial institutions. In summary, here’s what you should keep in mind:

  • Commit or pass. Landing a top tier client gives you market credibility but only if you win them. Be prepared to devote your entire executive team to winning this deal and seriously evaluate the opportunity cost versus the probability of win.
  • Stay true to your vision. Tier 1 firms will give you incredible insight on the power of your solution, however it’s not always aligned with your vision. Augmenting your solution to meet their needs is expected, but don’t allow yourself to transition your entire business model for their unique requirements.
  • Don’t be lazy. Winning top tier firms is a lot of work; do it! Shortcutting the process never works. Most importantly, turn your main contact into an inside coach, personalize every presentation, document assumptions and explain their return-on-investment.


What’s Next

Hopefully, you adhere to some of this advice and before you know it, that big contract comes in! Just as you’re ready to pop the champagne, you’ll make eye contact with your Head of Client Onboarding and notice tears in their eyes. Yes, onboarding Tier 1 firms is difficult, time-consuming and can easily go off-track. In our next post in this Elephant Hunting Series, we will provide practical advice on to effectively manage and control the onboarding of top tier accounts. However, we all know it doesn’t stop once the client goes live, so our last post in this series will focus on the Client Success function and how to ensure user adoption from your largest clients.

Happy elephant hunting!


About Linda

Linda Wittich formed Top Line Focus in October 2019 as a strategic advisory and consultancy firm for mid-stage fintech startups to help them grow FASTER. She was confident that the tools she developed while rolling out 13 different first-of-a-kind SaaS products at firms like Finn AI, IBM Watson for Wealth, Doxim, Broadridge, NSCC/DTCC, and Citi, could be applied to help mid-stage startups.

Her plan is working! She led WealthForge (Altigo) through its growth spurt of 50x transaction volume and 15x sales growth and Marstone’s introduction of two new first-of-a-kind products while shortening their median client onboarding cycle by over 60% and some onboardings by more than 90%.

For more information, email linda@toplinefocus.com.





The Wealth Tech Today blog is published by Craig Iskowitz, founder and CEO of Ezra Group, a boutique consulting firm that caters to banks, broker-dealers, RIA’s, asset managers and the leading vendors in the surrounding #fintech space. He can be reached at craig@ezragroupllc.com