Selling into the Enterprise: Practical Advice for Early Stage Teams

Last week, Venture Guides hosted Alla Piltser, an infrastructure technology leader with three decades of experience selecting and managing enterprise tools and vendors in the financial services industry. This fireside chat, hosted by Leigh Moore from Venture Guides, focused on key strategies for early-stage founders looking to break into enterprise markets. Alla shared guidance and first-hand experience about the purchasing process with local Boston founders and sales leaders, along with a virtual audience, sharing what works, and what to avoid, in the enterprise selling process.  

For those who couldn't join us, here are some of our key takeaways:  

1. Solve Business Problems; Don’t Just Sell Technology

Alla emphasized that enterprise buyers are more concerned with solving concrete business problems than acquiring cutting-edge technology for its own sake. She highlighted that in sectors like finance, healthcare, and manufacturing, technology must address both business needs and regulatory requirements. Early-stage companies can stand out by ensuring their products address specific pain points and compliance needs, which are paramount in regulated industries.

2. Position Your Solution for Risk Management and ROI

Alla shared that large enterprises focus heavily on risk management and ROI when considering new technology investments. Solutions that mitigate risk—especially cybersecurity risks or regulatory gaps—are highly prioritized. If a startup can address a regulatory “matter requiring attention” (MRA), it can create a sense of urgency that accelerates the sales process. Startups should also clearly demonstrate the potential ROI of their solution, especially compared to legacy systems, as a differentiator.

3. Craft a Unique and Differentiated Message

In a crowded market, Alla advised startups to hone a narrow, unique value proposition that focuses on specific, unmet needs. Large enterprise customers are also looking for cost efficiency; established vendors often bring expansive, expensive solutions, leaving room for startups to offer more targeted and affordable alternatives. Highlighting unique capabilities, scalability, and cost savings can help smaller companies differentiate their offering.

4. Build Trust to Overcome Hesitancy Towards Startups

Winning the trust of enterprise buyers is critical. Startups must demonstrate reliability, build lasting relationships, and show they can scale. Alla encouraged founders to think beyond transactional sales and emphasize partnership, with consistent communication and a commitment to the customer’s success. Proving that your solution can simplify the portfolio or cut costs without sacrificing quality or compliance is also a plus.

5. Navigate Decision Committees and Stakeholders

Enterprise sales often involve numerous decision-makers. Alla pointed out that startups must engage with multiple stakeholders, including security, cloud operations, and audit teams. Tailoring the message to each group’s specific interests is essential. For example, while risk mitigation may appeal to security teams, cost savings and operational efficiency might resonate with infrastructure teams.

6. Maintain Visibility and Consistency

Alla highlighted the importance of staying top-of-mind, even if the buyer requests a delay. Regular check-ins with valuable updates—such as sharing a recent award, a case study, or testimonials from similar clients—can reinforce the solution’s relevance and build momentum for future sales discussions. Founders should balance persistence with respect for the buyer’s time, ensuring they remain visible and relevant without overwhelming the prospect

Alla’s insights underscore that while startups have unique challenges when selling to large enterprises, they also have unique opportunities. By aligning their technology with pressing business needs, demonstrating measurable ROI, and building trust through consistency and tailored communication, early-stage founders can successfully make inroads into the enterprise market. Thank you Alla for sharing this insight!