20Sales Why Everyone is Responsible for Demand Generation, How to do Great Sales Discovery, How to Reduce Sales Cycles and Create Urgency and Deal Reviews; Good and Bad Reasons to Lose a Deal with Doug Adamic, CRO @ Brex

Summary Notes


In this episode of "20 Sales," host Harry Stebbings is joined by Doug Adamick, CRO at Brex, to delve into the intricacies of sales strategy and execution. Doug, with his extensive background at SAP Concur, shares insights on the three reasons organizations make purchases and emphasizes the importance of selling value over features. He discusses the critical role of listening in sales, the necessity of creating constructive tension, and the significance of understanding a company's unique business problems to tailor solutions effectively. Doug also touches on the evolving nature of sales due to AI, the balance between industry and segment experience in building sales teams, and the importance of not being surprised by lost deals. Furthermore, he highlights the impact of Salesforce.com's sales strategy and the role of platforms like Outreach and Zoom Info in enhancing sales productivity and data-driven decision-making.

Summary Notes

Reasons Organizations Make Purchases

  • Organizations purchase for three main reasons: current troubles, anticipated troubles, or individuals/groups aiming to excel.
  • Understanding these reasons is crucial for sales teams to unlock revenue and engage effectively with potential buyers.

So there's only three reasons why an organization will make a purchase. They're in trouble right now. They see trouble coming, or an individual or group wants to be made a hero and get ahead of something.

This quote highlights the primary motivations behind organizational purchasing decisions, which are essential for sales strategies.

Introduction to the Show and Guest

  • The show "20 sales" focuses on sales leadership and strategies in tech companies.
  • Doug Adamick, CRO at Brex, is introduced as a seasoned leader with a significant track record at SAP Concur.
  • The episode also mentions Outreach and Zoom Info as key tools for sales productivity and efficiency.

This is 20 sales, the monthly show where sit down with the best sales leaders in the world to reveal their tips, tactics and strategies when it comes to starting and scaling sales teams.

This quote introduces the show's purpose, emphasizing the value of insights from top sales leaders like Doug Adamick.

Doug Adamick's Entry into Sales

  • Doug did not start in sales; he transitioned from finance and accounting after a suggestion from a friend.
  • His first sales job at Sintos provided excellent training, and he discovered a passion for the complexities and rewards of sales.

I didn't get into sales coming out of college. I was actually in finance and accounting... And the second I got into that organization, met the people and started to understand what sales was all about, I fell in love immediately.

Doug reflects on his unexpected entry into sales and his immediate affinity for the field upon experiencing it firsthand.

The Importance of Listening in Sales

  • Doug is recognized for his exceptional listening skills during sales calls.
  • Good listening involves genuine interest, mindfulness, and the absence of preconceived notions.
  • This approach helps in truly understanding and potentially improving a client's business.

He asks questions and listens. He asks another and listens. And in total, he says about 50 words in an hour long call.

Harry's observation of Doug's listening technique underscores its importance in sales communication and relationship building.

Sales Calls and Coaching

  • Doug records sales calls for review and coaching.
  • The enablement department breaks down the sales methodology into steps for better analysis and improvement.
  • The goal is to gain unique information and align the buying criteria with the solution offered.

When I break sales calls down, I break it down into how much are we listening? What kind of discovery questions are we asking?

Doug explains his methodical approach to dissecting sales calls to enhance the sales process and outcomes.

Doug's Aphorisms and Sales Philosophy

  • Doug emphasizes that pipeline creation is everyone's responsibility, not just the marketing department's.
  • His three objectives for go-to-market teams are demand creation, profitable pipeline conversion, and customer base growth and protection.
  • He advocates for quality over quantity in pipeline development, focusing on conversion rates and effective messaging.

Pipeline is our air. Without it, we die... Everything begins with everybody pitching in to create pipeline and demand.

Doug's quote illustrates the vital importance of pipeline generation for the survival and growth of a sales organization.

Effective Goal Setting for Pipeline and Revenue

  • Doug starts with identifying the sources of pipeline creation and then assesses the attributes and quality of the pipeline.
  • The objective is not just to create a large pipeline but to have one that effectively converts to revenue.
  • Understanding the conversion rates of different channels and messages helps in fine-tuning the pipeline strategy.

It's not the abundance of pipeline, it's the quality of the pipeline from source, by conversion, by channel, and then you can be able to dial in from there.

This quote highlights Doug's focus on the quality and strategic sourcing of the pipeline to drive revenue.

Driving High-Quality Pipeline

  • Content, product marketing, and positioning are crucial for communicating with various personas within an organization.
  • Accurate lead scoring and data hygiene are essential for monitoring and utilizing pipeline data.
  • The pipeline process is data-driven and requires careful analysis of conversion trends.

So at Brex, because of the business that we're in, a project can be initiated by a number of different constituents or personas within an organization at multiple different levels for multiple different reasons.

Doug outlines the complexity of the pipeline in relation to various business personas and the importance of tailored content and data accuracy.

Demand Creation in Challenging Times

  • Doug challenges the notion that demand creation is harder in tough times, seeing it as an opportunity to provide value.
  • He believes in a mindset focused on value-driven investments, which has led to successful pipeline building at Brex.
  • Doug also notes the increased difficulty in lead conversion and the importance of understanding patterns and timing in the sales process.

The tighter the times are, the more they need to pay attention to this. So I guess it's a mindset. We're building pipeline incredible right now going through that because of the times that they're in.

This quote reflects Doug's optimistic approach to demand creation during economic downturns, emphasizing the importance of mindset and strategy.

Concluding Remarks

  • The conversation wraps up with a humorous exchange about Doug's unique sayings, or "aphorisms."
  • Doug's insights throughout the conversation provide valuable lessons for sales professionals.

Don't get too herky jerky and getting too early because you'll fling them off the hook. You've got to let it set a little bit and then get them at the right time.

This final quote from Doug serves as a metaphor for the patience and strategy required in nurturing leads and closing sales.

Precision in Sales Campaigns

  • A properly run sales campaign begins at the first interaction ("hello").
  • Precision is critical in convincing and hooking multiple people within a company.
  • A salesperson often has only one chance to make an impression, as companies today are less likely to give second or third chances.
  • Every word and action in a sales campaign must be precise and lead towards the desired outcome.
  • The analogy of tossing a thread through multiple needles is used to illustrate the level of precision required.

"So when I'm talking with and coaching my, either leaders or my sales folks or all of the contributing departments that are there, I don't think that people recognize that a properly run sales campaign begins at hello."

This quote emphasizes the importance of the initial interaction in a sales campaign and the need for precision from the very beginning.

Identifying the Actual Buyer

  • To identify a true buyer, ask them about their experience implementing a similar product or service.
  • A precise and concise answer about their buying experience indicates you are likely speaking to the buyer.
  • Understanding organizational buying patterns is crucial for salespeople to avoid being misled.
  • Sales training should include how to recognize and speak to the actual buyer within an organization.

"Well, first of all, in a very, very pragmatic sense, asking that individual the last time they implemented something similar to Brex, and then just listen."

This quote suggests a practical approach to identifying whether the person you are speaking to has the authority and experience to make purchasing decisions.

Creating Multiple Champions in Sales

  • Constructive tension is necessary in sales to push the boundaries of the customer's thinking.
  • To create multiple champions, a salesperson must introduce a specific solution that drives outcomes not fully understood by the customer.
  • The process should help the customer quickly decide if they want to invest more time in discovering the solution or not.
  • Pushing the customer is sometimes needed to help them understand the value of the product or service being offered.

"It's a difficult one because you have to be okay with constructive tension in a sales campaign."

This quote addresses the challenge of creating multiple champions without making the process feel transactional and emphasizes the need for constructive tension.

Constructive Tension in Different Company Sizes

  • Constructive tension is challenging to achieve in both large and startup companies.
  • Larger organizations have complex layers, such as politics and history.
  • Startups have different patterns, but the need for constructive tension exists in both environments.

"No. It's interesting. I would say that both are difficult to be able to pull off."

This quote acknowledges that constructive tension is a universal challenge in sales, regardless of the size or type of company.

Sales Effectiveness and Financial Outcomes

  • Sales effectiveness is tied to the ability to make more frequent and larger financial deposits.
  • Following a sales playbook and rules can increase a salesperson's capacity to sell more.
  • The goal is to work more efficiently to make a better living, even as territories shrink and quotas increase.

"If I do my job correctly and you lean in on the playbook and you follow the rules that have been set up, technically, you should be able to get more done in a day."

This quote connects sales effectiveness to the potential for greater financial gains, highlighting the importance of adhering to established sales strategies.

Challenges in Adopting Effective Sales Behaviors

  • Sales reps may force deals if they don't take their effectiveness seriously.
  • It's crucial for sales reps to evaluate their activities and focus on those that lead to more frequent and larger financial returns.
  • Sales leaders should be available to help reps reduce inefficiencies and improve their sales activities.

"So when I'm hopeful, reps hear that, they're, like, making decisions on the activity they're doing directly in front of them and saying, does this get me closer to going to the bank to make larger deposits more frequently, or is this taking me away from that?"

This quote highlights the importance of sales reps critically assessing their activities to ensure they align with their financial goals.

Creating Urgency in the Sales Process

  • A strong value proposition is key to creating urgency.
  • Articulating the financial impact of waiting to address a problem can create urgency.
  • Deep discovery and multiple interviews help reveal immediate or upcoming issues that require addressing.
  • Organizations typically make purchases when in trouble, anticipating trouble, or seeking transformation.

"So the shortest answer for that is that you have a value proposition that's either going to save the company money, make the company money, save time, or do something so dramatic that waiting another day or another week has a financial impact on that."

This quote outlines how a compelling value proposition can create a sense of urgency in the sales process.

Discounting as a Sales Strategy

  • Discounting should be used cautiously, as it sets a precedent for the buying pattern.
  • Salespeople should stand by the value established for their product or service if they have done the necessary groundwork.
  • The focus should be on increasing average deal size, shortening cycle times, and improving pipeline conversion rates rather than discounting.

"Discounting is a difficult thing because you always want to charge what is fair for the value that you're bringing."

This quote advises against frequent discounting and emphasizes the importance of maintaining the value of the product or service.

Lengthening Stride and Quickening Step

  • The concept of "lengthen your stride and quicken your step" is a metaphor for increasing efficiency and speed in sales.
  • Sales reps must adapt to higher quotas and smaller territories by working smarter and faster.
  • Identifying and removing bottlenecks can help sales reps improve their performance.

"So when I say this, when quotas go up and territory shrink, that's the definition of growth. Then the only way for you to be able to make more money is to go faster."

This quote encapsulates the need for sales reps to adapt and improve their efficiency in the face of growing performance expectations.

Bottlenecks in Sales Performance

  • The biggest bottleneck is often a rep's understanding of the company's purpose and desired outcomes.
  • Sales reps should focus on changing buying criteria to align with their product, rather than leading with product features.
  • Understanding how a customer's business operates is essential for sales success.

"So if you don't understand how to change the buying criteria to lead to your product, rather than leading with your product, then I think that's the biggest challenge."

This quote identifies the primary challenge for sales reps as focusing too much on product features instead of how the product can meet the customer's needs.

Definition of Sales Playbook

  • A sales playbook provides a structured approach to running effective campaigns and ensuring a delightful customer experience.
  • It includes specific steps and sequences, with criteria that must be met before progressing to the next stage.
  • Adherence to the playbook is crucial as skipping steps can negatively impact the potential partnership.
  • The playbook is not about tricking companies but about ensuring steps are not missed, which could jeopardize the promised delivery.

"For me, a general sales playbook is the fact that in order for whatever segment you're talking about, to run an effective campaign that provides a delightful customer experience, where we explore whether or not there's potential for a partnership, you need to do these particular things in this particular sequence."

This quote emphasizes the importance of following a structured sequence of actions to ensure a successful and delightful customer experience during a campaign, which is essential for exploring potential partnerships.

Transitioning Between Sales Playbooks

  • Sales playbooks need to be adapted as an organization grows and stages change from pre-product/market fit (PMF) to post-PMF and scaling.
  • Signals for changing playbooks can be daily or weekly, indicating the need for tweaks.
  • A dedicated department catalogs signals for playbook changes, which are introduced at the start of a quarter or on a half-year or full-year basis to avoid disrupting business continuity.

"So how I handle it is that one of the departments that we built actually catalogs those things. And then when they build up to a specific level of residue, we figure out when is the right time to be able to augment the playbook and then be able to re enable the teams and introduce that on a regular basis."

This quote explains the process of monitoring for signals that indicate a need to adjust the sales playbook and the systematic approach to implementing changes without disrupting ongoing business operations.

Motivating Teams at the Start of a Quarter

  • Encouraging teams involves aligning personal goals with professional advancement.
  • It's critical to communicate the rarity and opportunity of the current environment and resources available to the team.
  • The goal is to help team members reach their fullest potential and recognize the unique moment they are in to capitalize on it.

"And do you have an awareness of how rare it is to be at a company like Brex during this moment in time, to have this incredible resourcing, tooling and ingenuity around you?"

This quote underscores the motivational strategy of making team members aware of the exceptional resources and opportunities at their disposal, which should be leveraged to achieve personal and professional goals.

Executive Involvement in Sales

  • Executive sponsorship is important for marquee organizations but does not always require the CEO's involvement.
  • The executive leadership team should participate in the go-to-market and sales process, with a balanced distribution of responsibilities.

"But if I'm holding myself accountable as a CRO, we will want to have executive sponsorship with all of our marquee organizations."

This quote highlights the role of executive leadership, particularly the Chief Revenue Officer (CRO), in ensuring executive sponsorship for important client relationships, without necessarily needing the CEO for every interaction.

Handoff to Customer Success (CS)

  • The handoff to CS begins with understanding the entire customer lifecycle.
  • It involves capturing relevant information during the sales campaign and passing it to the implementation team.
  • The transition to CS is smooth when the sales rep and readiness team work closely with the implementation team, and CS is introduced during this process.

"The sales rep and the readiness team stay very close at hand. Sales rep peels off. The customer success is introduced during the implementation process."

This quote describes the collaborative approach required during the handoff from the sales team to customer success, ensuring continuity and a clear understanding of the customer's needs and expectations.

Proving Return on Investment (ROI)

  • It's essential to prove ROI with data and case studies, especially when upselling.
  • The CS team structure may need to change to meet the expanding needs for proof of ROI.
  • Trust is built by focusing on driving business outcomes important to the customer, not the selling company.

"You're only as good as the last promise you made and fulfilled with an organization making sure that you're driving business outcomes that are important to the company, not for you."

This quote conveys the importance of fulfilling promises and focusing on the customer's business outcomes to maintain trust and foster a valuable relationship.

Deal Reviews

  • Deal reviews are conducted by frontline managers who aggregate information for their teams.
  • The process includes discussing organizational challenges, coverage models, and data received.
  • It's important to identify good and bad reasons for losing deals, with surprises being an inexcusable reason.

"The only reason that I get furious when we lose a deal is when we're surprised."

This quote emphasizes that surprises are unacceptable in deal reviews, as thorough analysis and understanding should prevent unexpected losses.

Anticipating Financial Challenges in Sales

  • Sales leaders must anticipate and understand the financial status of the organizations they sell to.
  • Knowing whether a prospect needs funding or is financially stable is crucial.
  • The depth of the value proposition should be weighed against any potential uncontrollable events.

"To not know what the financial aspect or pattern is of the organization you're selling to is inexcusable."

This quote stresses the critical nature of understanding a prospect's financial situation as part of the sales process to avoid unexpected obstacles.

Key Theme: Sales Forecasting and Predictability

  • Acknowledging the inevitability of sales slippage and the importance of managing expectations.
  • The significance of understanding timelines and holding both the sales team and customers accountable.
  • Constructive tension in early discussions to gauge customer commitment and create predictability in sales pipelines.
  • The role of close plans and setting expectations upfront to increase the probability of keeping deals within the quarter.

"The reality is you can't close everything every quarter, and not everything is always going to go your way. So this is always going to happen. However, it is materially triaged."

This quote emphasizes the acceptance of occasional setbacks in sales and the need for strategic handling of such situations to minimize their impact.

"You have to have those discussions in constructive tension at the beginning of the campaign to understand whether or not the customer is just shopping or whether they're actually looking to solve a problem..."

The quote highlights the necessity of discerning a customer's true intent early in the sales process to ensure efficient resource allocation and improve the likelihood of closing deals within the desired timeframe.

Key Theme: Human Element in Sales Leadership

  • Recognition of the unpredictable nature of human behavior in the sales process.
  • The challenge of managing a large team and numerous customer interactions.
  • The impact of personal circumstances on professional commitments and the resulting unpredictability.

"I think that as prepared as you can be and as organized or as thoughtful that you can be, it's still people. And we are a human wrapper around a world class product..."

This quote reflects on the human aspects of sales leadership, acknowledging that despite meticulous planning, the unpredictability of human behavior can still influence outcomes.

Key Theme: Evolution of Sales Leadership

  • The shift from individual sales performance to building systems and infrastructure that enable team success.
  • The importance of focusing on the processes that indirectly lead to achieving sales quotas.
  • The philosophy of prioritizing foundational work over direct pursuit of end-goals.

"And now I find joy in building systems and departments and infrastructure where the output or the result of the byproduct of that is always crushing your quota."

This quote illustrates the speaker's evolved perspective on leadership, valuing the creation of supportive structures that lead to consistent team success over individual accolades.

Key Theme: Hiring for Sales Teams

  • The balance between industry experience and fresh perspectives in sales hires.
  • The value of having team members with both segment experience and a willingness to innovate without preconceived notions.
  • The necessity of a diverse team to drive innovative sales campaigns and distribution models.

"So when you can balance some experience with the right type of person, with someone who has segment experience but not industry experience, that's when you get your best, most innovative and sort of interesting sales campaigns and structure and distribution models, in my opinion."

This quote suggests that a mix of experienced individuals and those new to the industry can create a dynamic and effective sales team capable of innovative approaches.

Key Theme: Common Mistakes in Sales Hiring

  • Founders and sales leaders often overestimate a salesperson's ability to run campaigns and position value independently.
  • Underestimating the importance of support, enablement, and tooling for salespeople.
  • The necessity of a collaborative environment to enhance sales performance.

"A salesperson unto themselves aren't going to sell well on average. They need to be supported by a team of people that tools them correctly..."

This quote points out the misconception that salespeople can excel without the proper support structure, emphasizing the need for a collaborative environment.

Key Theme: Impact of AI on Sales

  • AI's transformative potential in sales through pattern recognition, speech recognition, and outreach automation.
  • The excitement around using AI to reduce friction and increase efficiency in sales activities.
  • The balance between technology and the human aspect in complex sales scenarios.

"It's going to transform how and what and why we go about doing our business in the very near future, for sure."

The speaker expresses a strong belief in AI's imminent and significant impact on the sales industry, indicating a transformative shift in practices and methodologies.

Key Theme: Sales Tactics and Strategies

  • The consistency of selling value as a core sales tactic.
  • The outdated approach of leading with features and functionality due to more informed buyers.
  • The decreased effectiveness of traditional relationship-building tactics like corporate hospitality due to policy changes.
  • The increasing value of challenging customers' ideas and providing insightful perspectives.

"Selling value, in my opinion."

A concise affirmation that despite changes in the industry, the fundamental tactic of selling value remains unchanged.

"But what we're seeing is that customers will value you challenging their ideas or their status quo by being able to bring insights or views that are pushing the boundaries."

This quote highlights a shift in customer relationships, where value is now seen in the ability to challenge and improve upon a customer's current operations or thinking.

Key Theme: Advice for New Sales Leaders

  • The importance of understanding and influencing buying criteria to lead prospects to your product.
  • Setting up the sales team for success by aligning prospects' needs with the product's unique offerings.

"That you understand what buying criteria needs to change with your prospects in order for that to lead to your product."

The speaker advises new sales leaders to focus on how they can shift buying criteria in favor of their product to ensure successful sales outcomes.

Key Theme: Changing Perspectives on Sales

  • The desire to alter the negative stereotypes associated with salespeople.
  • The aspiration to recognize sales as a consultative profession that drives business improvement.

"Probably just the perspective that salespeople are smarmy or something like that."

This quote reveals the speaker's wish to change the common negative perception of salespeople into a more positive and professional image.

Key Theme: Maintaining Morale After Missed Quarters

  • Conducting a deep dive analysis after a missed quarter.
  • Focusing on positive indicators and reinforcing adherence to systems and processes.
  • The importance of not allowing setbacks to disrupt the long-term strategy and morale.

"So it's the positive reinforcement that lean in on the system and the playbook and that those things are going to pay off in the long term."

The speaker emphasizes the need for positive reinforcement and trust in the established systems to maintain morale and ensure future success, even after a disappointing quarter.

Key Theme: Impressive Sales Strategies

  • Admiration for Salesforce.com's approach to selling value and creating a customer success motion.
  • The comprehensive value Salesforce.com provides to its customers and its impact on the industry.

"I still am impressed by salesforce.com and how they go about getting business, how they sell value, the way in which they create an experience and a customer success motion for the companies that they have..."

The speaker expresses respect for Salesforce.com's sales strategy, citing it as a gold standard in the industry and a model to aspire to.

Key Theme: Reflection on the Discussion

  • Appreciation for the engaging and thought-provoking conversation.
  • Recognition of the host's preparation and research efforts.

"Thank you so much Harry. This has been a blast. I love getting to know you. The questions are great."

The speaker expresses gratitude towards the host for a rewarding and enjoyable discussion, highlighting the quality of the interaction.

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