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While they are all important, I'd put the PO over the other agile-specific roles as without an effective PO, the team won't build the right product. Also, finding someone with sufficient capacity, domain expertise and empowerment to play that role is quite challenging.
I would put on the same rank the Agile Coach/Scrum Master. He/she is helping the delivery team self-govern and self-organize, serves as a facilitator, helps the product owner manage the product backlog and communicate the projects vision.
My experience with "Agility" have brought me to believe that many organizations want be agile but very few really understand what it really means.
It's a fancy word that is very popular but it doesn't mesh very well with organizations that are used to working in silos and have traditional waterfall methods of delivery or reporting.
Finding the right balance requires a lot of effort and there is a fairly significant change in the organizational mindset of management which needs to take place if the move from Waterfall to Agile is to be successful.
I believe in the importance of the role, for large organisations, but considering the empirical nature of Agile I believe that it is hard to grow in that role.
The famous 'mindset change' should start at the pointy head and usually it doesn't. They still expect progress reports, accurate estimations and to be the only ones that take real decisions.
In case of a transformation to agile, from my point of view the most senior executive who demands the transformation is the most important role beside the change team leader and the change team, as this team will be the heart of the transformation.
Ranked by Importance:
1) Executive Sponsorship: If leadership doesn't drive it, it won't happen.
2) Agile Coach/Consultant: Someone with real experience to help the team transition. Getting a certification is not enough and is probably the most dangerous thing to have.
3) Product Owners: A Dedicated/Allocated Business Rep who understands and embraces this role will help the team deliver the right product.
Having done several Agile transformations the Executive sponsorship relevant to the scale of implementation is critical. A good rule of thumb is to get buy-in from at least 2 levels above the group you're converting. If you're converting all of IT then the CIO and CEO better have buy-in (if not the entire board) or else you're going to have real obstacles when it comes to HR.
The second most important role is a good Agile Coach or Consultant - and please don't use one of the "big boys" like PWC, Deloitte, Accenture, etc... as they tend to have LESS experience and are more rigid than more specialized companies and consultants. The Agile Coach will help you navigate obstacles and foresee challenges that an average CSM will not. When it comes to transformation, this ability to navigate and anticipate is critical to larger scale success.
The last more important role(s) are allocated Product Owners. Since this role sits with the business, this is usually the hardest to get because it needs to be a SME within the business which usually means this person was great at what they did, but now they have to transition OUT of that former role and into this one. Most organizations don't let them transition out, they just add more responsibility to this person. This is a huge mistake and the second leading cause behind transformation failure (behind no executive ownership).
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