Intro 0s
- Brendon Cassidy expresses excitement about the upcoming discussion.
- Cassidy and the host acknowledge that it has been a while since they last met.
Brendon’s Background 45s
- Cassidy entered the tech world around 1999-2000, starting his career as a recruiter during the dot-com bubble.
- The dot-com bubble burst led to a collapse in the recruiting industry, forcing Cassidy and his colleagues to adapt and reinvent themselves.
- Cassidy highlights the importance of adaptability and convincing others of one's expertise, which became essential skills during that challenging time.
- Despite their lack of experience, Cassidy and his colleagues went on to achieve significant success in their careers.
Changing Landscape of Sales 3m27s
- The traditional sales strategies and tactics are no longer effective.
- The focus has shifted to unlearning bad habits and adapting to new market conditions.
- The old customer acquisition costs are no longer relevant.
- Outbound sales and marketing models have become obsolete.
- Startups are now laser-focused on break-even, profitability, and long-term sustainability.
The Decline of Outbound SDR Model 5m36s
- The outbound SDR model is no longer effective due to market saturation and competition.
- There is a need for new and innovative ways to reach customers.
- Leveraging relationships, influence, and referrals can be an effective way to accelerate growth.
- Many companies are still operating with outdated outbound SDR models due to a lack of better alternatives.
- The current market conditions make it difficult to create personalized outbound marketing campaigns that stand out from the competition.
Impact of AI on Outbound Sales 7m17s
- AI's impact on outbound sales is significant and complex.
- The shift of demand generation from marketing to sales has caused problems.
- Great VP of sales are unlikely to accept jobs in companies that rely on an outbound go-to-market model for growth.
- Many founders cannot clearly articulate the problem their company aims to solve or why they are the ones to solve it.
Defining a Sales Playbook 9m5s
- A sales playbook is not a canned response but varies depending on the company and its circumstances.
- It should be rooted in understanding the customer's thinking, pain, psychology, personal opportunities, fears, and upside.
- Brendon Cassidy believes in selling to a person, not a company.
- Spending hours doing discovery calls is unnecessary if the salesperson has already researched and understood the customer's problems and psychology.
Importance of Customer Understanding 10m36s
- Understanding customers is crucial as their problems and pain points are finite.
- Knowing the different paths and potential turn-offs helps in effective customer conversations.
- VPS sales can be improved by deeply understanding the customer's perspective and needs.
- Knowing the customer's world and true pain points is essential for successful sales conversations.
- Great teams have a mapped-out understanding of their customers, avoiding unexpected challenges during calls.
How Discovery Should be Like 12m20s
- Discovery should be a means to an end, not a prolonged process.
- Discovery should be limited to 5 minutes, indicating a lack of effort in understanding customers if it takes longer.
- Teams should map out and execute the sales process within a 30-45 minute call.
- Founders should create a loosely built Playbook outlining successful strategies and approaches.
- The VPS team should eventually write the detailed Playbook based on their experiences.
Hiring VP of Sales First vs. Sales Reps 14m36s
- Founders should be actively involved in early sales.
- Hiring a VP of sales as the first sales hire is not recommended.
- Founders who lack sales experience may need to reconsider their assumptions.
- Successful SaaS companies often have active founders in early go-to-market.
Hiring Multiple Sales Reps at Once 15m26s
- Hiring two sales reps at a time can be advantageous.
- Hiring two different types of people can be beneficial.
- It's difficult to assess salespeople accurately.
- Salespeople are often not entirely honest on their resumes.
- Hiring sales reps "off the street" is risky.
- The odds of finding successful sales reps through online job boards are low.
- For the first five sales hires, it's best to rely on referrals from trusted individuals.
- Investors are not always reliable sources for hiring recommendations.
- Advisors or influencers in the industry can provide valuable recommendations.
- Consider forming a five-person advisory team to assist with hiring.
Structuring the Hiring Process for Sales Reps 19m32s
- Always have candidates do a demo or mock sales call based on what they currently sell.
- A panel of experienced sales hires should unanimously approve the candidate's pitch.
- This creates a high standard, but it ensures that candidates can effectively sell their product.
- For SDRs, focus on hiring individuals with coachable characteristics and potential for growth.
- After the first three to five hires, focus on aptitude, talent, coachability, ambition, and work ethic.
- Avoid hiring individuals with extensive experience in large tech companies, as their skills may not be transferable to a startup environment.
- Look for candidates who are willing to take on the challenge of convincing prospects that their problem is legitimate and worth solving.
Financial Incentives for Sales Reps 23m44s
- Pay sales reps a high percentage after they cover their operational costs.
- This ensures that sales reps are profitable and not a cost center.
- The EchoSign model is a good example of this type of compensation structure.
Common Mistakes in Hiring Sales Reps 25m24s
- Expecting to hire successful sales reps off the street can lead to a high turnover rate.
- Signs that a sales rep is not working out include:
- The founder feels the need to take over and run calls for them.
- The sales rep does not seem to be improving over time.
- Running a tight monthly sales process helps prevent sales reps from pushing deals out and making false commitments.
Onboarding Sales Reps 27m19s
- Give new sales reps time and training to onboard effectively.
- Founders should initially accompany new reps on sales calls to provide guidance and support.
- Utilize sales call recordings and demos for reps to analyze and learn from.
- Encourage reps to listen to relevant sales calls to gain insights into the sales cycle.
- Consider using a tool like Gong to facilitate call analysis and learning.
Firing Sales Reps 29m5s
- Avoid adhering to a strict "fire fast" philosophy without considering individual circumstances.
- If multiple sales reps are being fired quickly, it may indicate broader issues beyond individual performance.
- A quarter plus some change is a reasonable timeframe to assess a rep's progress.
- By the end of the second quarter, a rep should be fully ramped up.
- If a rep falls short in their first quarter and shows no improvement in the second quarter, consider letting them go.
Brendon’s Biggest Mistakes in Hiring 29m57s
- Enticed by resumes and experiences that may not reflect current abilities.
- Hired someone who looked great on paper but turned out to be a poor fit for the company culture and performance.
- Realized that investing in and promoting proven internal talent is more effective than hiring externally.
- Emphasized the importance of hiring people who have sold within the same ballpark of price point, sales cycle, and velocity.
- Hiring someone with a very different sales background can create tension and a high failure rate.
Deal Reviews 34m27s
- Brendon Cassidy shares his approach to conducting efficient deal reviews.
- He emphasizes the importance of monthly reviews, where salespeople commit to deals and identify potential deals.
- Cassidy highlights the correlation between customer communication and the likelihood of a deal closing.
- He suggests that a lack of communication for more than three days indicates potential issues with a deal.
- Cassidy stresses the need for constant communication with customers throughout the sales process.
Dealing with Lost Deals 36m47s
- To increase the chances of winning deals, it's crucial to be present at every layer of the deal, from the C-suite to the evaluators, decision-makers, and users.
- Losing a deal is usually not about what was done wrong in the final stages, but rather about what wasn't done or established earlier in the sales cycle.
- When a partner recommends someone, it's important to do your own due diligence and not rely solely on the partner's recommendation.
- Brendon Cassidy won a deal against DocuSign by focusing on every evaluator and user, while DocuSign relied solely on their partnership with Salesforce.
- Cassidy's strategy of checking in on every evaluator and user daily and rehearsing witness statements with them proved to be successful in winning the deal.
Quick-Fire Round 43m32s
- Sales tactics that have not changed in the last five years:
- Salespeople dependent on an SDR team to drive their own deal flow will always be successful.
- Sales tactics that have died:
- Outbound SDR model is declining.
- AI will likely take over demand generation, which most VPS of sales do not want to own.
- What Brendon would most like to change about the world of sales:
- He wants to see a world where startups start their sales process as close to the customer as possible to mitigate risk.
- He does not believe in the traditional methods of sending mass emails and making thousands of calls.
- Company sales strategy that Brendon has been most impressed by recently:
- Rippling:
- CRO used to work with Brendon at EchoSign.
- Has built a super team.
- Talkdesk:
- Adjusted to the current market conditions and is now doing well.
- Lantern:
- A Rippling for the sales Cloud type of play.
- Incredible early founders and traction.
- General observations about the market:
- When the market is down, there is a bounce in early-stage startups and founders.
- Super talented people tend to flow into the early-stage world when the risk is mitigated between a big company and a startup.
